Rhodium(III)-catalyzed [3+2] annulative coupling between oximes and electron-deficient alkynes

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• 作者：Xukai Zhou ; Songjie Yu ; Zisong Qi ; Xingwei Li
• 关键词：rhodium(III) ; C ; H activation ; annulation ; oxime ; alkyne
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2015
• 出版时间：August 2015
• 年：2015
• 卷：58
• 期：8
• 页码：1297-1301
• 全文大小：892 KB
• 参考文献：1.Bohme TM, Keim C, Kreutzmann K, Linder M, Dingermann T, Dannhardt G, Mutschler E, Lambrecht G. Structure-activity relationships of dimethindene derivatives as new M2-selective muscarinic receptor antagonists. J Med Chem, 2003, 46: 856鈥?67View Article
  2 a).Cheng YJ, Hsieh CH, He Y, Hsu CS, Li Y. Combination of indene-C60 bis-adduct and cross-linked fullerene interlayer leading to highly efficient inverted polymer solar cells. J Am Chem Soc, 2010, 132: 17381鈥?7383View Article
  2 b).He Y, Chen HY, Hou J, Li Y. Indene-C60 bisadduct: a new acceptor for high-performance polymer solar cells. J Am Chem Soc, 2010, 132: 1377鈥?382View Article
  2 c).Zhao G, He Y, Li Y. 6.5% Efficiency of polymer solar cells based on poly(3-hexylthiophene) and indene-C60 bisadduct by device optimization. Adv Mater, 2010, 22: 4355鈥?358View Article
  3.O鈥橞rien X, Parker J, Lessard P, Sinskey A. Engineering an indene bioconversion process for the production of cis-aminoindanol: a model system for the production of chiral synthons. Appl Microbiol Biotechnol, 2002, 59: 389鈥?99View Article
  4 a).Ackermann L, Vicente R, Kapdi AR. Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage. Angew Chem Int Ed, 2009, 48: 9792鈥?826View Article
  4 b).Arockiam PB, Bruneau C, Dixneuf PH. Ruthenium(II)-catalyzed C-H bond activation and functionalization. Chem Rev, 2012, 112: 5879鈥?918View Article
  4 c).Chen X, Engle KM, Wang DH, Yu JQ. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality. Angew Chem Int Ed, 2009, 48: 5094鈥?115View Article
  4 d).Cho SH, Kim JY, Kwak J, Chang S. Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation. Chem Soc Rev, 2011, 40: 5068鈥?083View Article
  4 e).Engle KM, Mei TS, Wasa M, Yu JQ. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions. Acc Chem Res, 2011, 45: 788鈥?02View Article
  4 f).Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Beyond directing groups: transition-metalcatalyzed C-H activation of simple arenes. Angew Chem Int Ed, 2012, 51: 10236鈥?0254View Article
  4 g).Song G, Wang F, Li X. C-C C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation. Chem Soc Rev, 2012, 41: 3651鈥?678View Article
  4 h).Sun CL, Li BJ, Shi ZJ. Pd-catalyzed oxidative coupling with organometallic reagents via C-H activation. Chem Commun, 2010, 46: 677鈥?85View Article
  4 i).Wencel-Delord J, Droge T, Liu F, Glorius F. Towards mild metal-catalyzed C-H bond activation. Chem Soc Rev, 2011, 40: 4740鈥?761View Article
  4 j).Wencel-Delord J, Glorius F. C-H bond activation enables the rapid construction and late-stage diversification of functional molecules. Nat Chem, 2013, 5: 369鈥?75View Article
  5 a).Kuninobu Y, Kawata A, Takai K. Rhenium-catalyzed formation of indene frameworks via C-H bond activation: [3+2] annulation of aromatic aldimines and acetylenes. J Am Chem Soc, 2005, 127: 13498鈥?3499View Article
  5 b).Kuninobu Y, Tokunaga Y, Kawata A, Takai K. Insertion of polar and nonpolar unsaturated molecules into carbonrhenium bonds generated by C-H bond activation: synthesis of phthalimidine and indene derivatives. J Am Chem Soc, 2006, 128: 202鈥?09View Article
  6.Sun ZM, Chen SP, Zhao P. Tertiary carbinamine synthesis by rhodium-catalyzed [3+2] annulation of N-unsubstituted aromatic ketimines and alkynes. Chem-Eur J, 2010, 16: 2619鈥?627View Article
  7.Tran DN, Cramer N. Enantioselective Rhodium(I)-catalyzed [3+2] annulations of aromatic ketimines induced by directed C-H activations. Angew Chem Int Ed, 2011, 50: 11098鈥?1102View Article
  8.Zhao P, Wang F, Han K, Li X. Ruthenium- and sulfonamide-catalyzed cyclization between N-sulfonyl imines and alkynes. Org Lett, 2012, 14: 5506鈥?509View Article
  9 a).Tran DN, Cramer N. Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic allenes by the [3+2] annulation of aryl ketimines. Angew Chem Int Ed, 2013, 52: 10630鈥?0634View Article
  9 b).Zhang J, Ugrinov A, Zhao P. Ruthenium(II)/ N-heterocyclic carbene catalyzed [3+2] carbocyclization with aromatic N-H ketimines and internal alkynes. Angew Chem Int Ed, 2013, 52: 6681鈥?684View Article
  9 c).Liu W, Zell D, John M, Ackermann L. Manganese-catalyzed synthesis of cis-b-amino acid esters through organometallic C-H activation of ketimines. Angew Chem Int Ed, 2015, doi: 10.1002/anie.201411808
  9 d).Shi XY, Li CJ. Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds. Org Lett, 2013, 15: 1476鈥?479View Article
  9 e).Seoane A, Casanova N, Qui帽ones N, Mascare帽as JL, Gul铆as M. Rhodium(III)-catalyzed dearomatizing (3+2) annulation of 2-alkenylphenols and alkynes. J Am Chem Soc, 2014, 136: 7607鈥?610View Article
  9 f).Zhou MB, Pi R, Hu M, Yang Y, Song RJ, Xia Y, Li JH. Rhodium(III)-catalyzed [3+2] annulation of 5-aryl-2,3-dihydro-1H-pyrroles with internal alkynes through C(sp2)-H/alkene functionalization. Angew Chem Int Ed, 2014, 53: 11338鈥?1341View Article
  9 g).Huang JR, Song Q, Zhu YQ, Qin L, Qian ZY, Dong L. Rhodium(III)-catalyzed three-component reaction of imines alkynes, and aldehydes through C-H activation. Chem-Eur J, 2014, 20: 16882鈥?6886View Article
  9 h).Dong L, Qu CH, Huang JR, Zhang W, Zhang QR, Deng JG. Rhodium-catalyzed spirocyclic sultam synthesis by [3+2] annulation with cyclic N-sulfonyl ketimines and alkynes. Chem-Eur J, 2013, 19: 16537鈥?6540View Article
  10.Patureau FW, Besset T, Kuhl N, Glorius F. Diverse strategies toward indenol and fulvene derivatives: Rh-catalyzed C-H activation of aryl ketones followed by coupling with internal alkynes. J Am Chem Soc, 2011, 133: 2154鈥?156View Article
  11.Muralirajan K, Parthasarathy K, Cheng CH. Regioselective synthesis of indenols by rhodium-catalyzed C-H activation and carbocyclization of aryl ketones and alkynes. Angew Chem Int Ed, 2011, 50: 4169鈥?172View Article
  12.Li BJ, Wang HY, Zhu QL, Shi ZJ. Rhodium/copper-catalyzed annulation of benzimides with internal alkynes: indenone synthesis through sequential C-H and C-N cleavage. Angew Chem Int Ed, 2012, 51: 3948鈥?952View Article
  13.Chen Y, Wang F, Zhen W, Li X. Rhodium(III)-catalyzed annulation of azomethine ylides with alkynes via C-H activation. Adv Synth Catal, 2013, 355: 353鈥?59
  14 a).Fukutani T, Umeda N, Hirano K, Satoh T, Miura M. Rhodiumcatalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage. Chem Commun, 2009: 5141鈥?143
  14 b).Chinnagolla RK, Jeganmohan M. Ruthenium-catalyzed regioselective cyclization of aromatic ketones with alkynes: an efficient route to indenols and benzofulvenes. Eur J Org Chem, 2012, 2012: 417鈥?23View Article
  14 c).Nagamoto M, Nishimura T. Catalytic [3+2] annulation of ketimines with alkynes via C-H activation by a cationic iridium(cod) complex. Chem Commun, 2014, 50: 6274鈥?277View Article
  15.Zhang XS, Chen K, Shi ZJ. Transition metal-catalyzed direct nucleophilic addition of C-H bonds to carbon-heteroatom double bonds. Chem Sci, 2014, 5: 2146鈥?159View Article
  16 a).Li L, Brennessel WW, Jones WD. An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M=Rh Ir). J Am Chem Soc, 2008, 130: 12414鈥?2419View Article
  16 b).Zhang X, Chen D, Zhao M, Zhao J, Jia A, Li X. Synthesis of isoquinolines via rhodium(III)-catalyzed dehydrative C-C and C-N coupling between oximines and alkynes. Adv Synth Catal, 2011, 353: 719鈥?23View Article
  16 c).Jayakumar J, Parthasarathy K, Chen YH, Lee TH, Chuang SC, Cheng CH. One-pot synthesis of highly substituted polyheteroaromatic compounds by rhodium(III)-catalyzed multiple C-H activation and annulation. Angew Chem Int Ed, 2014, 53: 9889鈥?892View Article
  16 d).Parthasarathy K, Cheng CH. Easy access to isoquinolines and tetrahydroquinolines from ketoximes and alkynes via rhodium-catalyzed C-H bond activation. J Org Chem, 2009, 74: 9359鈥?364View Article
  16 e).Chinnagolla RK, Pimparkar S, Jeganmohan M. Ruthenium-catalyzed highly regioselective cyclization of ketoximes with alkynes by C-H bond activation: a practical route to synthesize substituted isoquinolines. Org Lett, 2012, 14: 3032鈥?035View Article
  16 f).Too PC, Wang YF, Chiba S. Rhodium(III)-catalyzed synthesis of isoquino-lines from aryl ketone O-acyloxime derivatives and internal alkynes. Org Lett, 2010, 12: 5688鈥?691View Article
  16 g).Kornhaa脽 C, Li J, Ackermann L. Cationic ruthenium catalysts for alkyne annulations with oximes by C-H/N-O functionalizations. J Org Chem, 2012, 77: 9190鈥?198View Article
  17 a).Li X, Yu S, Wang F, Wan B, Yu X. Rhodium(III)-catalyzed C-C coupling between arenes and aziridines by C-H activation. Angew Chem Int Ed, 2013, 52: 2577鈥?580View Article
  17 b).Wang F, Song G, Li X. Rh(III)-catalyzed tandem oxidative olefination-michael reactions between aryl carboxamides and alkenes. Org Lett, 2010, 12: 5430鈥?433View Article
  17 c).Xie F, Qi Z, Li X. Rhodium(III)-catalyzed azidation and nitration of arenes by C-H activation. Angew Chem Int Ed, 2013, 52: 11862鈥?1866View Article
  18.Hyster TK, Rovis T. Pyridine synthesis from oximes and alkynesviarhodium(III) catalysis: Cp* and Cpt provide complementary selectivity. Chem Commun, 2011, 47: 11846鈥?1848View Article
  
• 作者单位：Xukai Zhou (1)
  Songjie Yu (1)
  Zisong Qi (1)
  Xingwei Li (1)
  
  1. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chinese Library of Science
  Chemistry
  
• 出版者：Science China Press, co-published with Springer
• ISSN：1869-1870

文摘

Rhodium(III)-catalyzed coupling between ketoximes and alkynes via C-H activation and annulation typically followed the [4+2] selectivity to afford isoquinolines. By designing alkynes bearing a highly electron-withdrawing group and under substrate control, we have successfully switched the selectivity of the coupling between oximes and alkynes to the alternative [3+2] annulation, leading to the efficient synthesis of indenamines. This process features good regioselectivity for both substrates, high efficiency, broad substrate scope, and excellent functional group tolerance.