钯催化的烯丙基碳酸酯与芳基硼酸的Suzuki-Miyaura偶联反应
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摘要
自从1979年,Suzuki与Miyaura开发了交叉偶联反应以来,该反应作为重要的碳碳键构筑方法受到了科学家们的广泛研究并被成功地运用于工业化。近30年以来,成功实现了一系列亲电试剂,如烯基,芳基,烷基,炔基等与有机硼酸试剂的交叉偶联反应,但是对于烯丙基类亲电试剂的报道却很少,而且已报导的烯丙基类亲电试剂,主要局限于伯烯丙基衍生物与芳基硼酸类化合物的偶联反应。1,3-不对称二取代烯丙醇类化合物与芳基硼酸的偶联反应可提供具有手性碳原子的烯丙基芳基类化合物,且该类化合物是很多重要天然化合物的结构单元,但此类烯丙基-芳基偶联反应的研究却很少。因此开发高效、高选择性的1,3-不对称二取代烯丙醇类化合物与芳基硼酸的偶联反应具有重要的学术及现实意义。
本论文,我们开发了第一例通用的钯催化的利用1,3-不对称二取代的烯丙基碳酸酯与芳基硼酸的Suzuki?Miyaura偶联反应。反应在金属钯催化下,含水的有机溶剂里,在不添加碱的情况下,以高的收率、优越的化学、区域及顺反选择性地得到了烯丙基-芳基偶联的产物。该反应具有广泛的普适性,适合于各种1,3-不对称二取代的烯丙基碳酸酯类化合物与多种芳基硼酸类化合物的交叉偶联。同时我们对反应的立体化学进行了研究,当利用手性烯丙基碳酸酯为原料,反应实现了完美的手性转移并得到了构型翻转的产物。我们将此烯丙基-芳基偶联反应成功地应用到了抗炎镇痛药物(S)-萘普生的合成中。通过我们的研究,有效地拓宽了Suzuki?Miyaura偶联反应的应用范围,并提供了一种高效、方便、实际的烯丙基-芳基偶联反应的合成方法学。
Since Suzuki-Miyaura coupling reaction was explored by Suzuki and Miyaura in 1979, it has been considered by scientists as a powerful method for C-C bond formation and successfully used for industry. Over the past thirty years, a broad range of electrophiles undergoing cross-couplings with organoboronic acids, including alkyl, aryl, alkenyl, and alkynyl groups have been widely reported. However, the coupling reaction with allylic derivatives has been rarely reported, and most of the reports, the allylic partners have been confined to primary allylic halides or alcohol derivatives. The coupling reaction of unsymmetric 1,3-disubstituted secondary allylic derivatives with arylboronic acids could afford the allylic partners with chiral carbon atoms, in addition, there are a lot of significant natural compounds which all contain this kind of coupling framework, but it is rarely reported. So it makes great sense of exploring a highly efficient and selective method for the coupling reaction of unsymmetric 1,3-disubstituted secondary allylic derivatives with arylboronic acids
In my thesis,we represent the first general method for Pd-catalyzed Suzuki?Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids. The Pd-catalyzed reaction has been developed in the wet solvent under base free system to afford allyl?aryl coupling products in high level of isolated yields with complete regio- and E/Z selectivities with good to excellent chemoselectivities. The reaction reveals wide generality and is suitable for the cross-coupling of various unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids. The stereochemical course of the coupling reaction has been demonstrated that are excellent chirality transfer with inversion of the stereochemistry, and the coupling reaction was successfully applied to the synthesis of (S)-Naproxen.
Our studies effectively extend the scope of Suzuki?Miyaura coupling reaction and provide a simple, convenient and practical protocol for allyl?aryl coupling.
本论文,我们开发了第一例通用的钯催化的利用1,3-不对称二取代的烯丙基碳酸酯与芳基硼酸的Suzuki?Miyaura偶联反应。反应在金属钯催化下,含水的有机溶剂里,在不添加碱的情况下,以高的收率、优越的化学、区域及顺反选择性地得到了烯丙基-芳基偶联的产物。该反应具有广泛的普适性,适合于各种1,3-不对称二取代的烯丙基碳酸酯类化合物与多种芳基硼酸类化合物的交叉偶联。同时我们对反应的立体化学进行了研究,当利用手性烯丙基碳酸酯为原料,反应实现了完美的手性转移并得到了构型翻转的产物。我们将此烯丙基-芳基偶联反应成功地应用到了抗炎镇痛药物(S)-萘普生的合成中。通过我们的研究,有效地拓宽了Suzuki?Miyaura偶联反应的应用范围,并提供了一种高效、方便、实际的烯丙基-芳基偶联反应的合成方法学。
Since Suzuki-Miyaura coupling reaction was explored by Suzuki and Miyaura in 1979, it has been considered by scientists as a powerful method for C-C bond formation and successfully used for industry. Over the past thirty years, a broad range of electrophiles undergoing cross-couplings with organoboronic acids, including alkyl, aryl, alkenyl, and alkynyl groups have been widely reported. However, the coupling reaction with allylic derivatives has been rarely reported, and most of the reports, the allylic partners have been confined to primary allylic halides or alcohol derivatives. The coupling reaction of unsymmetric 1,3-disubstituted secondary allylic derivatives with arylboronic acids could afford the allylic partners with chiral carbon atoms, in addition, there are a lot of significant natural compounds which all contain this kind of coupling framework, but it is rarely reported. So it makes great sense of exploring a highly efficient and selective method for the coupling reaction of unsymmetric 1,3-disubstituted secondary allylic derivatives with arylboronic acids
In my thesis,we represent the first general method for Pd-catalyzed Suzuki?Miyaura coupling reaction of unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids. The Pd-catalyzed reaction has been developed in the wet solvent under base free system to afford allyl?aryl coupling products in high level of isolated yields with complete regio- and E/Z selectivities with good to excellent chemoselectivities. The reaction reveals wide generality and is suitable for the cross-coupling of various unsymmetric 1,3-disubstituted secondary allylic carbonates with arylboronic acids. The stereochemical course of the coupling reaction has been demonstrated that are excellent chirality transfer with inversion of the stereochemistry, and the coupling reaction was successfully applied to the synthesis of (S)-Naproxen.
Our studies effectively extend the scope of Suzuki?Miyaura coupling reaction and provide a simple, convenient and practical protocol for allyl?aryl coupling.
引文
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[2] Negishi Reaction, see reviews: (a) Herrmann, W. A.; ?fele, K.; Preysing, D.; Schneider, S. J. Organomet. Chem. 2003, 687, 229. (b) Newkome, G.; Patri, A.; Holder, E.; Schubert, U. Eur. J. Org. Chem. 2004, 235. (c) Negishi, E.; Wang, G.; Rao, H.; Xu, Z. J. Org. Chem. 2010, 75, 3151. (d) Wagner, M. Angew. Chem. Int. Ed. 2006, 45, 5916.
[3] Stille Reaction, see reviews: (a) McGlacken, G.; Fairlamb, I. Eur. J. Org. Chem. 2009, 4011. (b) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4442. (c) Espinet, P.; Echavarren, A. M. Angew. Chem. Int. Ed. 2004, 43, 4704. (d) Pattenden, G.; Sinclair, D. J. J. Organomet. Chem. 2002, 653, 261.
[4] Kumada Reaction, see reviews: (a) Li, B.?J.; Yu, D.?G.; Sun, C.?L.; Shi, Z.?J. Chem. Eur. J. 2011, 17, 1728. (b) Yu, D.?G.; Li, B.?J.; Shi, Z.?J. Acc. Chem. Res. 2010, 43, 1486. (c) Frost, C, G.; Mutton, L. Green Chem. 2010, 12, 1687. (d) Ford, L.; Jahn, U. Angew. Chem. Int. Ed. 2009, 48, 6386.
[5] Ullmann Reaction, see reviews: (a) Monnier, F.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 6954. (b) Monnier, F.; Taillefer, M. Angew. Chem. Int. Ed. 2008, 47, 3096. (c) Ozawa, F.; Yoshifuji, M. Dalton Trans. 2006, 4987. (d) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
[6] Suzuki-Miyaura, Reaction, see reviews: (a) Fu, G. C. Acc. Chem. Res. 2008, 41, 1555. (b) Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461. (c) Miyaura, N. Top. Curr. Chem. 2002, 219, 11. (d) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633. (e) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
[7] Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866.
[8] Miyaura, N.; Yanagi, A. Suzuki, Synth. Commun. 1981, 11, 513.
[9] Smith, G. B.; Dezeny, G. C.; Hughes, D. L.; King, D. L.; Verhoeven, T. R. J. Org. Chem. 1994, 59, 8151.
[10] Kamikawa, K.; Watanabe, T.; Daimon A.; Uemura, M. Tetrahedron 2000, 56, 2325.
[11] Jacks, T. E.; Belmont, D. T.; Briggs, C. A.; Horne, N. M.; Kanter, G. D.; Karrick, G. L.; Krikke, J. J.; McCabe, R. J.; Mustakis, J. G.; Nanninga, T. N.; Risedorph, G. S.; Seamans, R. E.; Skeenan, R. E.; Winkle, D. D.; Zennie, T. M. Org. Process Res. Dev. 2004, 8 , 201.
[12] Brandt, T. A.; Caron, S.; Damon, D. B.; DiBrino, J.; Ghosh, A.; Griffith, D. A.; Kedia, S.; Ragan, J. A.; Rose, P. R.; Vanderplas, B. C.; Wei, L. Tetrahedron 2009, 65, 3292;
[13] Glasnov, T. N.; Kappe, C. O. Adv. Synth. Catal. 2010, 352, 3089.
[14] Rudolph, A.; Lautens, M. Angew. Chem. Int. Ed. 2009, 48, 2656.
[15] Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691.
[16] Bedford, R. B.; Betham, M.; Coles, S. J.; Frost, R. M.; Hursthouse, M. B. Tetrahedron 2005, 61, 9663.
[17] Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
[18] Shi, Y.; Li, X.; Liu, J.; Jiang, W.; Sun. L. Appl. Organometal. Chem. 2011, 25, 514.
[19] Pigge, F. C. Synthesis 2010, 1745.
[20] Moreno-Manas, M.; Pajuelo, F.; Pleixats, R. J. Org. Chem. 1995, 60, 2396.
[21] Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Org. Lett. 2005, 7, 1829.
[22] Gerbino, D. C.; Mandolesi, S. D.; Schmalz, H.-G.; Podestá, J. C. Eur. J. Org. Chem. 2009, 3964.
[23] Kayaki, Y.; Koda, T.; Ikariya, T. Eur. J. Org. Chem. 2004, 4989.
[24] Tsukamoto, H.; Sato, M.; Kondo, Y. Chem. Commun. 2004, 1200.
[25] Manabe, K.; Nakada, K.; Aoyama, N.; Kobayashi, S. Adv. Synth. Catal. 2005, 347, 1499.
[26] Tsukamoto, H.; Uchiyama, T.; Suzuki, T.; Kondo, Y. Org. Biomol. Chem. 2008, 6, 3005.
[27] Nishikata, T.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 12103.
[28] Bouyssi, D.; Gerusz, V.; Balme, G. Eur. J. Org. Chem. 2002, 2445.
[29] Ortar, G. Tetrahedron Lett. 2003, 44, 4311.
[30] Nájera, C.; Gil-Moltó, J.; Karlstr?m, S. Adv. Synth. Catal. 2004, 346, 1798.
[31] Kabalka, G. W.; Al-Masum, M. Org. Lett., 2006, 8, 11.
[32] Mino, T.; Kajiwara, K.; Shirae, Y.; Sakamoto, M.; Fujita, T. Synlett. 2008, 2711.
[33] Yamada, Y. M.; Watanabe, T.; Torii, K.; Uozumi, Y. Chem. Commun. 2009, 5594.
[34] Kobayashi, Y.; Mizojiri, R.; Ikeda, E. J. Org. Chem. 1996, 61, 5391.
[35] Uozumi, Y.; Danjo, H.; Hayashi, T. J. Org. Chem. 1999, 64, 3384.
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