2-氰基-4'-甲基联苯的合成研究
|
摘要
2-氰基-4’-甲基联苯是制备沙坦类抗高血压药物的关键中间体。研究了以对氯甲苯和镁为原料,碘的引发下合成对甲苯基氯化镁中间体,再进一步与邻氯苯腈反应合成目标化合物的反应特性。
在对甲苯基氯化镁合成反应中,考察了反应中所用的原料、溶剂等因素,并用单因素法探索其优化反应条件。研究了不同溶剂对对甲苯基氯化镁产率的影响,在四氢呋喃与甲苯混合溶剂中,对甲苯基氯化镁产率为77.7%。在无水无氧条件下,以过渡金属(MnCl_2、CoCl_2、NiCl_2、CuCl_2、Ni(PPh_3)_2Cl_2、CdCl_2)为催化剂,以THF、甲苯或THF、甲苯混合溶剂为溶剂,对甲苯基氯化镁为反应中间体与邻氯苯腈偶联制得目标化合物。实验发现,MnCl(25 mol%)催化,THF溶剂中目标产物的产率为87.2%;混合溶剂中产率降为79.3%,减少了副产物的种类,提高了反应的选择性。讨论金属化合物催化剂作用下的合成反应特性和机理,提高产品选择性和收率并建立合适的纯化方法,使反应具有可实际操作性。对目标产物进行了~1HNMR、IR的结构表征。
2-cyano-4’-methylbiphenyl, which is a key intermediate used for the preparation of antihypertensive drugs, was synthesized by the couple of p-methyl phenylmagnesium chloride with o-chlorobenzonitrile.
In the reaction of p-metheylphenylmagnesium chloride, several factors including the species of materials, solvent were discussed through single-factor approach and the optimum reaction condition was obtained. GC yield of 77.7% p-tolylmagnesiumchloride intermediate in toluene-tetrahydrofuran mixed solvents was obtained based on internal standard analysis.
2-cyano-4’-methylbiphenyl was easily synthesized by the coupling of non-active o-chlorobenzonitrile with p-methylphenylmagnesium chloride in toluene-tetrahydrofuran mixed solvents over transition-metal catalysts(MnCl_2、CoCl_2、NiCl_2、CuCl_2、Ni(PPh_3)_2Cl_2、CdCl_2). Various reaction conditions, especially catalysis of some catalysts were discussed to improve selectivity suitable for industrialization in the recycle solvent system. The structures of target products-biphenyl compounds were characterized through 1HNMR and IR. In the coupling reaction, various reaction conditions, especially catalysis of some metal catalysts, were discussed to improve product yield and purity to meet commercial use.
在对甲苯基氯化镁合成反应中,考察了反应中所用的原料、溶剂等因素,并用单因素法探索其优化反应条件。研究了不同溶剂对对甲苯基氯化镁产率的影响,在四氢呋喃与甲苯混合溶剂中,对甲苯基氯化镁产率为77.7%。在无水无氧条件下,以过渡金属(MnCl_2、CoCl_2、NiCl_2、CuCl_2、Ni(PPh_3)_2Cl_2、CdCl_2)为催化剂,以THF、甲苯或THF、甲苯混合溶剂为溶剂,对甲苯基氯化镁为反应中间体与邻氯苯腈偶联制得目标化合物。实验发现,MnCl(25 mol%)催化,THF溶剂中目标产物的产率为87.2%;混合溶剂中产率降为79.3%,减少了副产物的种类,提高了反应的选择性。讨论金属化合物催化剂作用下的合成反应特性和机理,提高产品选择性和收率并建立合适的纯化方法,使反应具有可实际操作性。对目标产物进行了~1HNMR、IR的结构表征。
2-cyano-4’-methylbiphenyl, which is a key intermediate used for the preparation of antihypertensive drugs, was synthesized by the couple of p-methyl phenylmagnesium chloride with o-chlorobenzonitrile.
In the reaction of p-metheylphenylmagnesium chloride, several factors including the species of materials, solvent were discussed through single-factor approach and the optimum reaction condition was obtained. GC yield of 77.7% p-tolylmagnesiumchloride intermediate in toluene-tetrahydrofuran mixed solvents was obtained based on internal standard analysis.
2-cyano-4’-methylbiphenyl was easily synthesized by the coupling of non-active o-chlorobenzonitrile with p-methylphenylmagnesium chloride in toluene-tetrahydrofuran mixed solvents over transition-metal catalysts(MnCl_2、CoCl_2、NiCl_2、CuCl_2、Ni(PPh_3)_2Cl_2、CdCl_2). Various reaction conditions, especially catalysis of some catalysts were discussed to improve selectivity suitable for industrialization in the recycle solvent system. The structures of target products-biphenyl compounds were characterized through 1HNMR and IR. In the coupling reaction, various reaction conditions, especially catalysis of some metal catalysts, were discussed to improve product yield and purity to meet commercial use.
引文
[1] Carl, F. N.; Ulrike, K. S.; Martin, N.; Stefan, B. A new protocol for the one-pot synthesis of symmetrical biaryls[J]. J. Org. Chem., 2004, 69: 6830-6833.
[2] Tamura, M.; Kochi, J. K. Vinylation of gridnard reagents catalysis by iron[J]. J. Am. Chem. Soc., 1971, 98: 1487
[3] Inada, K.; Miyaura, N. Synthesis of biaryls via cross-coupling reaction of arylboronic acids with aryl chlorides catalyzed by NiCl2/triphenylphosphine complexes[J]. Tetrahedron, 2000, 56: 8657-8660.
[4] Xi, Z. X.; Liu, B.; Chen, W. Z. Room-temperature Kumada cross-coupling of unactivated aryl chlorides catalyzed by N-heterocylic carbene-based nikel(Ⅱ) complexes[J]. J. Org. Chem., 2008, 73: 3954-3957.
[5] Goossen, L. J.; Rodriguez, N.; Melze, R. B.; Linder, C.; Deng, G.; Levy, L. M. Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides[J]. J. Am. Chem. Soc., 2007, 129: 4824-4833.
[6] Goossen, L. J.; Melzer, B. Synthesis of valsartan via decarboxylative biaryl coupling[J]. J. Org. Chem., 2007, 72: 7473-7476.
[7] Yan, C. F.; McCurry, P. M. Selective carbon-carbon bond formation via transition metal catalysis.3.A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel-or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides[J]. J. Org. Chem., 1977, 42 (10): 1821-1823.
[8] Diego, A. A.; Carmen, N.; M, C. P. Highly active oxime-derived palladacycle complexes for suzuki-miyaura and ullmann-type coupling reactions[J]. J. Org. Chem., 2002, 67: 5588-5594.
[9] Gabriela, A. G.; Mihai. S. V.; Jinkun, H.; Chunming, Z.; Mark, L. T.; Steven. P. N. Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems[J]. Organometallics, 2002, 21: 2866-2873.
[10] Tolman, C. A.; Seidel, W. C.; Gerlach, D. H. Triarylphosphine and ethylene complexes of zerovalent nickel palladium and platinum[J]. J. Am. Chem. Soc., 1972, 4 (19): 2669-2676.
[11]徐守昌.有机化学.北京:高等教育出版社, 1996: 396.
[12] Adam, F. L.; Chaoyang, D.; Gregor, C. F. Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions[J]. J. Am. Chem. Soc., 2000, 122: 4020-4028.
[13] Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev., 1995, 95: 2475-2483.
[14] Torres, J. C.; Pinto, A. C.; Garden, S. J. Application of a catalytic palladium biaryl synthesis reaction via C-H functionalization, to the total synthesis of amaryllidaceae alkaloids[J]. Tetrahedron, 2004, 60: 9889-9900.
[15] Vade, M.; Nisbimura, M.; Miyaura, N. A palladium-catalyzed biaryl coupling of arylboronic acids in aqueous media using a gluconamide-substituted triphenylphosphine(GLCAphos) ligand[J]. Synlett, 2000, 6: 856-858.
[16] Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water[J]. J. Org. Chem., 2004, 69: 439-446.
[17] Negishi, E.; King, A. O.; Okukado, N. Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- or palladium- catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides[J]. J. Org. Chem., 1977, 42: 1821-1823.
[18] Xi, Z. X.; Zhang, X. M.; Chen, W. Z.; Fu, S. Z.; Wang, D. Q. Synthesis and structural characterization of nickel(Ⅱ) complexes supported by pyridine-functionalized N-heterocyclic carbene ligands and their catalytic activities for Suzuki coupling[J]. Organometallics, 2007, 26: 6636-6642.
[19] Kim, S. H.; Rieke, R. D. A facile synthetic method for the preparation of benzylic manganese halides using highly active manganese and their coupling reactions[J]. J. Org. Chem., 1998, 63: 6766-6767.
[20] Dominique, G.; Pascal, M.; Jean, R. D.; Patrice, M. New practical syntheses of 4’-methylbiphenyl-2-carbonitrile and -2-carbaldehyde[J]. J. Org. Chem., 1999, 64: 4516-4518.
[21] Grushin, V. V.; Alper, H. Transformation of chloroarenes, catalyzed by transition-metal complexes[J]. Chem. Rev., 1994, 94: 1047-1062.
[22] Chaoyang, D.; Gregory, C. F. The first general method for palladium-catalyzed negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)3)2 as a catalyst[J]. J. Am. Chem. Soc., 2001, 123: 2719-2724.
[23] Inada, K.; Miyaura, N. Synthesis of biaryls via cross-coupling reaction of arylboronic acids with aryl chlorides catalyzed by NiCl2/triphenylphosphinecomplexes[J]. Tetrahedron, 2000, 56: 8657-8660.
[24] Matinez-Barrasa, V.; Garcia, A.; Burgos, C.; Alvarez-Builla J. Synthesis of biaryls via intermolecular radical addition of heterarly and aryl bromides onto arenes[J]. Org. Lett., 2000, 24: 3933-3935.
[25]王玉炉主编.有机合成化学.科学出版社: 2005, 2: 86-89.
[26]向文军,胡海平,雷兴家,李飞.甲苯溶液中惰性卤代芳烃格氏试剂的制备[J].河北化工, 2007, 9 (30) : 27-28.
[27]李爱玲主编.有机化学,山东大学出版社, 2007: 80.
[28]高鸿宾主编.有机化学(第三版),高等教育出版社, 1999, 9 (3) : 186, 298.
[29] Miyaura, N.; Suzuki, A. palladium-catalyzed cross-coupling reacions of organoboron compounds[J]. Chem. Rev., 1995, 95 (7) : 2457-2483.
[30] Neguishi, E. Palladium- or nickel-catalyzed cross coupling. A new selective method for carbon-carbon bond formation[J]. Acc. Chem. Res., 1982, 15 (11): 340-348.
[31] Farina, V. New perspectives in the cross-coupling reactions of organostannanes[J]. Pure Appl. Chem., 1996, 68 (1): 73-78.
[32] Kumada, M. Nickel and palladium complex catalyzed cross-coupling reations of organometallic reagents with organic halides[J]. Pure Appl. Chem., 1980, 52: 669-679.
[33] Hatanaka, Y.; Hiyama, T. Highly selective cross-coupling reactions of organosilicon compounds mediated by fluoride ion and a palladium catalyst[J]. Synlett, 1991: 845-853.
[34]梁云,李金恒.钯催化卤代芳烃Ullmann偶联反应[J].有机化学, 2005, 2 (25) : 147-151.
[35] Kao, L. C.; Stakem, F. G.; Patel, S, B.; Heck, R. F. Palladium-catalyzed reactions of vinylic bromides with allylic alcohol and amine derivatives[J]. J. Org. Chem., Res. 1982, 47 (7): 1267-1277.
[36] Heck, R. F.; Bender, D, D.; Stakem, G. S. Palladium-catalyzed arylation and vinylation of 1, 4-dienes[J]. J. Org. Chem., 1982, 47(7): 1278- 1284.
[37] Burch, R. R.; Muetterties, E. L.; Teller, R. G.; Williams, J. M. Coordinately unsaturated clusters. A novel catalytic reaction. J. Am. Chem. Soc., 1982, 104 (15): 4257-4258.
[38] Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C.; Lemaire, M. Direct Homocoupling of aryl halides catalyzed by palladium[J]. Tetrahedron Lett., 1998, 39: 2559-2560.
[39] Hassan, J.; Penalva, V.; Lavenot, L.; Gozzi, C.; Lemaire, M. Catalytic alternative of the Ullmann reaction[J]. Tetrahedron, 1998, 54: 13793-13804.
[40] Mukhopadhyay, M.; Rothenberg, G.; Gitis, D.; Sasson, Y. On the mechanism of palladium-catalyzed coupling of haloaryls to biaryls in water with zinc[J]. Org. Lett., 2000, 2 (2):211-214.
[41] Semmelhack, M. F.; Brickener, S. T. Nickel-promoted cyclization/ carbonylation in the preparation of. Alpha. -methylene-. gamma. lactones. stereospecific synthesis of(.+-.)-frullanolide[J]. J. Am. Chem. Soc., 1981, 103 (13) : 3945-3947.
[42] Semmelhack, M. F.; Brickner, S. J. Intramolecular carbonylation of vinyl halides to form methylene lactones[J]. J. Org. Chem., 1981, 46 (8): 1723-1726.
[43] Semmelhack, M. F.; Helquist, P. M.; Jones, L. D.; Ryono, N. S. Reaction of aryl and vinyl halides with zerovalent nickel-preparative aspects and the synthesis of alnusone[J]. J. Am. Chem. Soc., 1981, 103: 6460- 6471.
[44] Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Generation of a solvated zerovalent nickel reagent[J]. Tetrahedron Lett., 1975, 16 (39): 3375-3378.
[45] Zembayashi, M.; Tamao, K.; Kumada, M. Nickel-phosphine complex-catalyzed homo coupling of aryl halides in the presence of zinc powder[J]. Tetrahedron Lett., 1977, 18 (47): 4089-4091.
[46] Lin, S. Z.; Chen, Q. A.; You, T. P. A novel nickel(0)-catalyzed cascade Ullmann-pinacol coupling: from o-bromobenzaldhyde to trans-9, 10-dihydroxy-9, 10-dihydrophenanthrene[J]. Synlett, 2007, 13: 2101-2105.
[47] Colon, I. Reduction of organic halides by water and zinc effected by nickel[J]. J. Org. Chem., 1982, 47 (13): 2622-2625.
[48]刘瑛,马啸华,马淮凌,黄华伟. 2-氰基-4’-甲基联苯的合成研究[J].化工时刊, 2006, 9 (9) : 48-49.
[49]常瑜,相会明,宋广慧,翟红. 2-氰基-4’-甲基联苯的合成[J].化工生产与技术, 2007, 14(4) : 31-33.
[50]秦海敏,喻宗沅,容如滨,邓嘉伦. 2-氰基-4’-甲基联苯的合成进展[J].化学与生物工程, 2007, 24(3) : 5-7.
[51]卢小逸,杨光新. 2-氰基-4’-甲基联苯的制备[J].中国医药工业杂志, 2005, 36(7): 396-397.
[52] David, J. C.; John, V. D.; Paul, E. A.; Andrew, T. C.; Alexander, L. J.; Michael, E. P.; William, A. P.; Joseph, B. S.; Gregory, J. W.; Ruth, R. W.; Pancras, C. W.; Sung-Eun, Y. Nonpeptide angiotensinⅡreceptorantagonists: the discovery of a series of N-(biphenylylmethyl)imidazoles as potent, orally active antihypertensives[J]. J. Med. Chem., 1991, 34(8): 2525-2547.
[53] Sain, B.; Sandhu; Jagir, S. A facile one-pot synthesis of unsymmetrical biaryl-2-carbonitriles by novel reaction of ylidenemalononitriles with dienamines[J]. J. Org. Chem., 1990, 55(8): 45-46.
[54]严琳,何阳明,陈群.催化偶联法合成2-氰基-4’-甲基联苯的工艺研究[J].化工时刊, 2007, 21(2): 18-20.
[55] Kageyama, H. Method for producting an asymmetric biaryl derivative[P]. EP 571770, 1993.; see also Chem. Abs., 125: 86-90.
[56] Akira, M.; Yuki, N.; Atsushi, A.; Motohiro, T.; Takuma, S. Potent, orally active imidazo[4, 5-b] pyridine-based angiotensinⅡreceptor antagonists[J]. J. Med. Chem., 1991, 34: 2919-2922.
[57] Miyaura, N.; Akira; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev., 1995, 95(7): 47-48.
[58] Herrmann, W. A.; Brossmer, C.; Oefele, K., Preysing, D. V.; Schneider, S, K. Palladacycles as structurally defined catalysts for the Heck olefination of chlora- and bromoarenes[J]. Angew. Chem. Int. Ed. Engl., 1995, 34(17): 44-47.
[59] Dominique, G.; Pascal, M.; Jean-Robert, D.; Patrice, M. New Practical Syntheses of 4’-methylbiphenyl-2-carbonitrile and 2-carbaldehyde[J]. J. Org. Chem., 1999, 64(12): 16-18.
[60] Ueda, M.; Nisbimura, M.; Miyaura, N.; A palladium-catalyzed biaryl coupling of arylboronic acids in aqueous media using a gluconamide-substituted triphenylphosphine(GLCAphos) ligand[J]. Synlett, 2000, (6): 56-58.
[61] Carlos, B.; Avelino, C.; Hermenegildo, G.; Antonio, L. Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water[J]. J. Org. Chem., 2004, 69(2): 39-46.
[62]张翘楚,郭梦萍. 2-氰基-4’-甲基联苯合成方法综述[J].中国医药工业杂志, 2007, 38 (11): 819-821.
[63]姚其正,张志祥,林宏志等. 2-氰基-4’-甲基联苯的合成方法的研究[J].药学进展, 2001, 25 (3): 49-52.
[64]王利民,邹刚.精细有机合成工艺.化学工业出版社, 2008: 25.
[65]诹访章,古井健夫.红土矿选择性氯化焙烧的研究[J].国外重有色金属,1964, 7: 8-10.
[66]陈梓云,彭梦侠.微波加热CoCl2·6H2O的脱水研究[J].山东化工, 2005, 36 (4): 9-10.
[67]巩育军,刘启瑞,张祝莲.乙醇溶解脱水法制备无水氯化铜的研究[J].延安大学学报(自然科学版), 1994, 12 (4): 45-49.
[68] Miller, J. A.;; Robert, P.; Farrell. Synthesis of functionally substituted unsymmetrical biaryls via a novel double metal catalyzed couplong reaction[J]. Tetrahedron Lett., 1998, 39: 7275-7278.
[69]姚印钦主编.高等学校使用教材,有机化学实验(第二版).武汉理工大学出版社, 2004, 01: 63-64.
[70] Chaoyang, D.; Gregory, C. F. The first general method for palladium-catalyzed negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)3)2 as a catalyst[J]. J. Am. Chem. Soc., 2001, 123: 2719-2724.
[71] Yoshiteru, H.; Dmitry, S. B.; Yuki, U.; Yasuji, S.; Takeshi, S. Highly selective sumthesis of 4, 4’-dimethylbiphenyl and its relevant spectroscopic study[J]. Ind. Eng. Chem. Res., 2005, 44: 2917-2920.
[72] Robert, E. B.; Edward, C. T. Cyclization reactions of 2,2’-disubstituted biphenyls[J]. Chem. Rev., 1968, 68 (2) : 209-227.
[2] Tamura, M.; Kochi, J. K. Vinylation of gridnard reagents catalysis by iron[J]. J. Am. Chem. Soc., 1971, 98: 1487
[3] Inada, K.; Miyaura, N. Synthesis of biaryls via cross-coupling reaction of arylboronic acids with aryl chlorides catalyzed by NiCl2/triphenylphosphine complexes[J]. Tetrahedron, 2000, 56: 8657-8660.
[4] Xi, Z. X.; Liu, B.; Chen, W. Z. Room-temperature Kumada cross-coupling of unactivated aryl chlorides catalyzed by N-heterocylic carbene-based nikel(Ⅱ) complexes[J]. J. Org. Chem., 2008, 73: 3954-3957.
[5] Goossen, L. J.; Rodriguez, N.; Melze, R. B.; Linder, C.; Deng, G.; Levy, L. M. Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides[J]. J. Am. Chem. Soc., 2007, 129: 4824-4833.
[6] Goossen, L. J.; Melzer, B. Synthesis of valsartan via decarboxylative biaryl coupling[J]. J. Org. Chem., 2007, 72: 7473-7476.
[7] Yan, C. F.; McCurry, P. M. Selective carbon-carbon bond formation via transition metal catalysis.3.A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel-or palladium-catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides[J]. J. Org. Chem., 1977, 42 (10): 1821-1823.
[8] Diego, A. A.; Carmen, N.; M, C. P. Highly active oxime-derived palladacycle complexes for suzuki-miyaura and ullmann-type coupling reactions[J]. J. Org. Chem., 2002, 67: 5588-5594.
[9] Gabriela, A. G.; Mihai. S. V.; Jinkun, H.; Chunming, Z.; Mark, L. T.; Steven. P. N. Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems[J]. Organometallics, 2002, 21: 2866-2873.
[10] Tolman, C. A.; Seidel, W. C.; Gerlach, D. H. Triarylphosphine and ethylene complexes of zerovalent nickel palladium and platinum[J]. J. Am. Chem. Soc., 1972, 4 (19): 2669-2676.
[11]徐守昌.有机化学.北京:高等教育出版社, 1996: 396.
[12] Adam, F. L.; Chaoyang, D.; Gregor, C. F. Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions[J]. J. Am. Chem. Soc., 2000, 122: 4020-4028.
[13] Miyaura, N.; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev., 1995, 95: 2475-2483.
[14] Torres, J. C.; Pinto, A. C.; Garden, S. J. Application of a catalytic palladium biaryl synthesis reaction via C-H functionalization, to the total synthesis of amaryllidaceae alkaloids[J]. Tetrahedron, 2004, 60: 9889-9900.
[15] Vade, M.; Nisbimura, M.; Miyaura, N. A palladium-catalyzed biaryl coupling of arylboronic acids in aqueous media using a gluconamide-substituted triphenylphosphine(GLCAphos) ligand[J]. Synlett, 2000, 6: 856-858.
[16] Baleizao, C.; Corma, A.; Garcia, H.; Leyva, A. Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water[J]. J. Org. Chem., 2004, 69: 439-446.
[17] Negishi, E.; King, A. O.; Okukado, N. Selective carbon-carbon bond formation via transition metal catalysis. 3. A highly selective synthesis of unsymmetrical biaryls and diarylmethanes by the nickel- or palladium- catalyzed reaction of aryl- and benzylzinc derivatives with aryl halides[J]. J. Org. Chem., 1977, 42: 1821-1823.
[18] Xi, Z. X.; Zhang, X. M.; Chen, W. Z.; Fu, S. Z.; Wang, D. Q. Synthesis and structural characterization of nickel(Ⅱ) complexes supported by pyridine-functionalized N-heterocyclic carbene ligands and their catalytic activities for Suzuki coupling[J]. Organometallics, 2007, 26: 6636-6642.
[19] Kim, S. H.; Rieke, R. D. A facile synthetic method for the preparation of benzylic manganese halides using highly active manganese and their coupling reactions[J]. J. Org. Chem., 1998, 63: 6766-6767.
[20] Dominique, G.; Pascal, M.; Jean, R. D.; Patrice, M. New practical syntheses of 4’-methylbiphenyl-2-carbonitrile and -2-carbaldehyde[J]. J. Org. Chem., 1999, 64: 4516-4518.
[21] Grushin, V. V.; Alper, H. Transformation of chloroarenes, catalyzed by transition-metal complexes[J]. Chem. Rev., 1994, 94: 1047-1062.
[22] Chaoyang, D.; Gregory, C. F. The first general method for palladium-catalyzed negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)3)2 as a catalyst[J]. J. Am. Chem. Soc., 2001, 123: 2719-2724.
[23] Inada, K.; Miyaura, N. Synthesis of biaryls via cross-coupling reaction of arylboronic acids with aryl chlorides catalyzed by NiCl2/triphenylphosphinecomplexes[J]. Tetrahedron, 2000, 56: 8657-8660.
[24] Matinez-Barrasa, V.; Garcia, A.; Burgos, C.; Alvarez-Builla J. Synthesis of biaryls via intermolecular radical addition of heterarly and aryl bromides onto arenes[J]. Org. Lett., 2000, 24: 3933-3935.
[25]王玉炉主编.有机合成化学.科学出版社: 2005, 2: 86-89.
[26]向文军,胡海平,雷兴家,李飞.甲苯溶液中惰性卤代芳烃格氏试剂的制备[J].河北化工, 2007, 9 (30) : 27-28.
[27]李爱玲主编.有机化学,山东大学出版社, 2007: 80.
[28]高鸿宾主编.有机化学(第三版),高等教育出版社, 1999, 9 (3) : 186, 298.
[29] Miyaura, N.; Suzuki, A. palladium-catalyzed cross-coupling reacions of organoboron compounds[J]. Chem. Rev., 1995, 95 (7) : 2457-2483.
[30] Neguishi, E. Palladium- or nickel-catalyzed cross coupling. A new selective method for carbon-carbon bond formation[J]. Acc. Chem. Res., 1982, 15 (11): 340-348.
[31] Farina, V. New perspectives in the cross-coupling reactions of organostannanes[J]. Pure Appl. Chem., 1996, 68 (1): 73-78.
[32] Kumada, M. Nickel and palladium complex catalyzed cross-coupling reations of organometallic reagents with organic halides[J]. Pure Appl. Chem., 1980, 52: 669-679.
[33] Hatanaka, Y.; Hiyama, T. Highly selective cross-coupling reactions of organosilicon compounds mediated by fluoride ion and a palladium catalyst[J]. Synlett, 1991: 845-853.
[34]梁云,李金恒.钯催化卤代芳烃Ullmann偶联反应[J].有机化学, 2005, 2 (25) : 147-151.
[35] Kao, L. C.; Stakem, F. G.; Patel, S, B.; Heck, R. F. Palladium-catalyzed reactions of vinylic bromides with allylic alcohol and amine derivatives[J]. J. Org. Chem., Res. 1982, 47 (7): 1267-1277.
[36] Heck, R. F.; Bender, D, D.; Stakem, G. S. Palladium-catalyzed arylation and vinylation of 1, 4-dienes[J]. J. Org. Chem., 1982, 47(7): 1278- 1284.
[37] Burch, R. R.; Muetterties, E. L.; Teller, R. G.; Williams, J. M. Coordinately unsaturated clusters. A novel catalytic reaction. J. Am. Chem. Soc., 1982, 104 (15): 4257-4258.
[38] Penalva, V.; Hassan, J.; Lavenot, L.; Gozzi, C.; Lemaire, M. Direct Homocoupling of aryl halides catalyzed by palladium[J]. Tetrahedron Lett., 1998, 39: 2559-2560.
[39] Hassan, J.; Penalva, V.; Lavenot, L.; Gozzi, C.; Lemaire, M. Catalytic alternative of the Ullmann reaction[J]. Tetrahedron, 1998, 54: 13793-13804.
[40] Mukhopadhyay, M.; Rothenberg, G.; Gitis, D.; Sasson, Y. On the mechanism of palladium-catalyzed coupling of haloaryls to biaryls in water with zinc[J]. Org. Lett., 2000, 2 (2):211-214.
[41] Semmelhack, M. F.; Brickener, S. T. Nickel-promoted cyclization/ carbonylation in the preparation of. Alpha. -methylene-. gamma. lactones. stereospecific synthesis of(.+-.)-frullanolide[J]. J. Am. Chem. Soc., 1981, 103 (13) : 3945-3947.
[42] Semmelhack, M. F.; Brickner, S. J. Intramolecular carbonylation of vinyl halides to form methylene lactones[J]. J. Org. Chem., 1981, 46 (8): 1723-1726.
[43] Semmelhack, M. F.; Helquist, P. M.; Jones, L. D.; Ryono, N. S. Reaction of aryl and vinyl halides with zerovalent nickel-preparative aspects and the synthesis of alnusone[J]. J. Am. Chem. Soc., 1981, 103: 6460- 6471.
[44] Kende, A. S.; Liebeskind, L. S.; Braitsch, D. M. Generation of a solvated zerovalent nickel reagent[J]. Tetrahedron Lett., 1975, 16 (39): 3375-3378.
[45] Zembayashi, M.; Tamao, K.; Kumada, M. Nickel-phosphine complex-catalyzed homo coupling of aryl halides in the presence of zinc powder[J]. Tetrahedron Lett., 1977, 18 (47): 4089-4091.
[46] Lin, S. Z.; Chen, Q. A.; You, T. P. A novel nickel(0)-catalyzed cascade Ullmann-pinacol coupling: from o-bromobenzaldhyde to trans-9, 10-dihydroxy-9, 10-dihydrophenanthrene[J]. Synlett, 2007, 13: 2101-2105.
[47] Colon, I. Reduction of organic halides by water and zinc effected by nickel[J]. J. Org. Chem., 1982, 47 (13): 2622-2625.
[48]刘瑛,马啸华,马淮凌,黄华伟. 2-氰基-4’-甲基联苯的合成研究[J].化工时刊, 2006, 9 (9) : 48-49.
[49]常瑜,相会明,宋广慧,翟红. 2-氰基-4’-甲基联苯的合成[J].化工生产与技术, 2007, 14(4) : 31-33.
[50]秦海敏,喻宗沅,容如滨,邓嘉伦. 2-氰基-4’-甲基联苯的合成进展[J].化学与生物工程, 2007, 24(3) : 5-7.
[51]卢小逸,杨光新. 2-氰基-4’-甲基联苯的制备[J].中国医药工业杂志, 2005, 36(7): 396-397.
[52] David, J. C.; John, V. D.; Paul, E. A.; Andrew, T. C.; Alexander, L. J.; Michael, E. P.; William, A. P.; Joseph, B. S.; Gregory, J. W.; Ruth, R. W.; Pancras, C. W.; Sung-Eun, Y. Nonpeptide angiotensinⅡreceptorantagonists: the discovery of a series of N-(biphenylylmethyl)imidazoles as potent, orally active antihypertensives[J]. J. Med. Chem., 1991, 34(8): 2525-2547.
[53] Sain, B.; Sandhu; Jagir, S. A facile one-pot synthesis of unsymmetrical biaryl-2-carbonitriles by novel reaction of ylidenemalononitriles with dienamines[J]. J. Org. Chem., 1990, 55(8): 45-46.
[54]严琳,何阳明,陈群.催化偶联法合成2-氰基-4’-甲基联苯的工艺研究[J].化工时刊, 2007, 21(2): 18-20.
[55] Kageyama, H. Method for producting an asymmetric biaryl derivative[P]. EP 571770, 1993.; see also Chem. Abs., 125: 86-90.
[56] Akira, M.; Yuki, N.; Atsushi, A.; Motohiro, T.; Takuma, S. Potent, orally active imidazo[4, 5-b] pyridine-based angiotensinⅡreceptor antagonists[J]. J. Med. Chem., 1991, 34: 2919-2922.
[57] Miyaura, N.; Akira; Suzuki, A. Palladium-catalyzed cross-coupling reactions of organoboron compounds[J]. Chem. Rev., 1995, 95(7): 47-48.
[58] Herrmann, W. A.; Brossmer, C.; Oefele, K., Preysing, D. V.; Schneider, S, K. Palladacycles as structurally defined catalysts for the Heck olefination of chlora- and bromoarenes[J]. Angew. Chem. Int. Ed. Engl., 1995, 34(17): 44-47.
[59] Dominique, G.; Pascal, M.; Jean-Robert, D.; Patrice, M. New Practical Syntheses of 4’-methylbiphenyl-2-carbonitrile and 2-carbaldehyde[J]. J. Org. Chem., 1999, 64(12): 16-18.
[60] Ueda, M.; Nisbimura, M.; Miyaura, N.; A palladium-catalyzed biaryl coupling of arylboronic acids in aqueous media using a gluconamide-substituted triphenylphosphine(GLCAphos) ligand[J]. Synlett, 2000, (6): 56-58.
[61] Carlos, B.; Avelino, C.; Hermenegildo, G.; Antonio, L. Oxime carbapalladacycle covalently anchored to high surface area inorganic supports or polymers as heterogeneous green catalysts for the Suzuki reaction in water[J]. J. Org. Chem., 2004, 69(2): 39-46.
[62]张翘楚,郭梦萍. 2-氰基-4’-甲基联苯合成方法综述[J].中国医药工业杂志, 2007, 38 (11): 819-821.
[63]姚其正,张志祥,林宏志等. 2-氰基-4’-甲基联苯的合成方法的研究[J].药学进展, 2001, 25 (3): 49-52.
[64]王利民,邹刚.精细有机合成工艺.化学工业出版社, 2008: 25.
[65]诹访章,古井健夫.红土矿选择性氯化焙烧的研究[J].国外重有色金属,1964, 7: 8-10.
[66]陈梓云,彭梦侠.微波加热CoCl2·6H2O的脱水研究[J].山东化工, 2005, 36 (4): 9-10.
[67]巩育军,刘启瑞,张祝莲.乙醇溶解脱水法制备无水氯化铜的研究[J].延安大学学报(自然科学版), 1994, 12 (4): 45-49.
[68] Miller, J. A.;; Robert, P.; Farrell. Synthesis of functionally substituted unsymmetrical biaryls via a novel double metal catalyzed couplong reaction[J]. Tetrahedron Lett., 1998, 39: 7275-7278.
[69]姚印钦主编.高等学校使用教材,有机化学实验(第二版).武汉理工大学出版社, 2004, 01: 63-64.
[70] Chaoyang, D.; Gregory, C. F. The first general method for palladium-catalyzed negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd(P(t-Bu)3)2 as a catalyst[J]. J. Am. Chem. Soc., 2001, 123: 2719-2724.
[71] Yoshiteru, H.; Dmitry, S. B.; Yuki, U.; Yasuji, S.; Takeshi, S. Highly selective sumthesis of 4, 4’-dimethylbiphenyl and its relevant spectroscopic study[J]. Ind. Eng. Chem. Res., 2005, 44: 2917-2920.
[72] Robert, E. B.; Edward, C. T. Cyclization reactions of 2,2’-disubstituted biphenyls[J]. Chem. Rev., 1968, 68 (2) : 209-227.