OALib Journal期刊
ISSN: 2333-9721
费用:99美元
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Rh(III)催化的N-甲氧基苯甲酰胺系列物选择性C-H氰基化反应
DOI: 10.1016/S1872-2067(15)60872-5, PP. 1175-1182
Keywords: Rh(III)催化剂,C-H键氰基化,N-甲氧基苯甲酰胺系列物,N-氰基-N-苯基对甲苯磺酰胺,反应机制
Abstract:
?采用了最近热门的Rh(III)催化C-H键活化方法,以N-甲氧基苯甲酰胺系列物为反应底物,N-氰基-N-苯基对甲苯磺酰胺(NCTS)为氰基化试剂,高效合成了含氰基官能团产物.结果表明,该反应在碳酸银存在下,使用二氧六环作为反应溶剂,于80℃反应8h生成的邻位氰基取代的N-甲氧基苯甲酰胺的产率较高.进一步研究表明,该反应具有好的区域选择性和底物/官能团适应性.一系列机理实验研究表明,该反应可能采用了一个内部的亲电取代机制及使用了C-H键切割步骤作为关键限速步骤.考虑到该反应产物包含有价值的结构单元-N-甲氧基甲酰胺和氰基取代基,因而有望用于现代有机合成中.
References
[1] | Ackermann L, Wang L H, Wolfram R, Lygin A V. Org Lett, 2012, 14: 728
|
[2] | Qi Z S, Wang M, Li X W. Chem Commun, 2014, 50: 9776
|
[3] | Duan P P, Lan X, Chen Y, Qian S S, Li J J, Lu L, Lu Y B, Chen B, Hong M, Zhao J. Chem Commun, 2014, 50: 12135
|
[4] | Shen Y Y, Liu G X, Zhou Z, Lu X Y. Org Lett, 2013, 15: 3366
|
[5] | Zhou J, Shi J J, Liu X L, Jia J L, Song H C, Xu H E, Yi W. Chem Commun, 2015, 51: 5868
|
[6] | Qi Z S, Li X W. Chin J Catal (戚自松, 李兴伟. 催化学报), 2015, 36: 48
|
[7] | Simmons E M, Hartwig J F. Angew Chem Int Ed, 2012, 51: 3066
|
[8] | Feng C, Loh T P. Angew Chem Int Ed, 2014, 53: 2722
|
[9] | Jones W D. Acc Chem Res, 2003, 36: 140
|
[10] | Kou X Z, Zhao M D, Qiao X X, Zhu Y M, Tong X F, Shen Z M. Chem Eur J, 2013, 19: 16880
|
[11] | Pan C D, Jin H M, Xu P, Liu X, Cheng Y X, Zhu C J. J Org Chem, 2013, 78: 9494
|
[12] | Xu H, Liu P T, Li Y H, Han F S. Org Lett, 2013, 15: 3354
|
[13] | Yang Y, Buchwald S L. Angew Chem Int Ed, 2014, 53: 8677
|
[14] | Xu L, Mou X Q, Chen Z M, Wang S H. Chem Commun, 2014, 50: 10676
|
[15] | Yan Y P, Yuan Y Z, Jiao N. Org Chem Front, 2014, 1: 1176
|
[16] | Gong T J, Xiao B, Cheng W M, Su W, Xu J, Liu Z J, Liu L, Fu Y. J Am Chem Soc, 2013, 135: 10630
|
[17] | Chaitanya M, Yadagiri D, Anbarasan P. Org Lett, 2013, 15: 4960
|
[18] | Chaitanya M, Anbarasan P. J Org Chem, 2015, 80: 3695
|
[19] | Gu L J, Jin C, Wang R, Ding H Y. ChemCatChem, 2014, 6: 1225
|
[20] | Han J, Pan C D, Jia X F, Zhu C J. Org Biomol Chem, 2014, 12: 8603
|
[21] | Hong X H, Wang H, Qian G Y, Tan Q T, Xu B. J Org Chem, 2014, 79: 3228
|
[22] | Lewis J C, Bergman R G, Ellman J A. Acc Chem Res, 2008, 41: 1013
|
[23] | Satoh T, Miura M. Chem Eur J, 2010, 16: 11212
|
[24] | Han Y F, Jin G X. Chem Soc Rev, 2014, 43: 2799
|
[25] | He R, Huang Z T, Zheng Q Y, Wang C. Tetrahedron Lett, 2014, 55: 5705
|
[26] | Song G Y, Li X W. Acc Chem Res, 2015, 48: 1007
|
[27] | Wang D H, Wasa M, Giri R, Yu J Q. J Am Chem Soc, 2008, 130: 7190
|
[28] | Wasa M, Yu J Q. J Am Chem Soc, 2008, 130: 14058
|
[29] | Guimond N, Gouliaras C, Fagnou K. J Am Chem Soc, 2010, 132: 6908
|
[30] | Wang G W, Yuan T T. J Org Chem, 2010, 75: 476
|
[31] | Karthikeyan J, Cheng C H. Angew Chem Int Ed, 2011, 50: 9880
|
[32] | Wrigglesworth J W, Cox B, Lloyd-Jones G C, Booker-Milburn K I. Org Lett, 2011, 13: 5326
|
[33] | Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc, 2011, 133: 2350
|
[34] | Guimond N, Gorelsky S I, Fagnou K. J Am Chem Soc, 2011, 133: 6449
|
[35] | Wang H G, Glorius F. Angew Chem Int Ed, 2012, 51: 7318
|
[36] | Zeng R, Fu C L, Ma S M. J Am Chem Soc, 2012, 134: 9597
|
[37] | Zeng R, Wu S Z, Fu C L, Ma S M. J Am Chem Soc, 2013, 135: 18284
|
[38] | Yang F Z, Ackermann L. J Org Chem, 2014, 79: 12070
|
[39] | Yang W, Sun J Q, Xu X X, Zhang Q, Liu Q. Chem Commun, 2014, 50: 4420
|
[40] | Liu Y J, Xu H, Kong W J, Shang M, Dai H X, Yu J Q. Nature, 2014, 515: 389
|
[41] | Yu D G, de Azambuja F, Glorius F. Angew Chem Int Ed, 2014, 53: 2754
|
[42] | Yang W, Wang S, Zhang Q, Liu Q, Xu X X. Chem Commun, 2015, 51: 661
|
[43] | Shi J J, Zhou J, Yan Y N, Jia J L, Liu X L, Song H C, Xu H E, Yi W. Chem Commun, 2015, 51: 668.
|
[44] | Oxgaard J, Tenn W J, Nielsen R J, Periana R A, Goddard W A. Or-ganometallics, 2007, 26: 1565
|
[45] | Ackermann L. Chem Rev, 2011, 111: 1315
|
[46] | Ma W B, Ackermann L. Chem Eur J, 2013, 19: 13925
|
[47] | Ma W B, Mei R H, Tenti G, Ackermann L. Chem Eur J, 2014, 20: 15248
|
[48] | Jia J L, Shi J J, Zhou J, Liu X L, Song Y L, Xu H E, Yi W. Chem Commun, 2015, 51: 2925
|
[49] | Ackermann L, Lygin A V. Org Lett, 2012, 14: 764
|
[50] | Ackermann L, Wang L H, Wolfram R, Lygin A V. Org Lett, 2012, 14: 728
|
[51] | Qi Z S, Wang M, Li X W. Chem Commun, 2014, 50: 9776
|
[52] | Duan P P, Lan X, Chen Y, Qian S S, Li J J, Lu L, Lu Y B, Chen B, Hong M, Zhao J. Chem Commun, 2014, 50: 12135
|
[53] | Shen Y Y, Liu G X, Zhou Z, Lu X Y. Org Lett, 2013, 15: 3366
|
[54] | Zhou J, Shi J J, Liu X L, Jia J L, Song H C, Xu H E, Yi W. Chem Commun, 2015, 51: 5868
|
[55] | Qi Z S, Li X W. Chin J Catal (戚自松, 李兴伟. 催化学报), 2015, 36: 48
|
[56] | Simmons E M, Hartwig J F. Angew Chem Int Ed, 2012, 51: 3066
|
[57] | Feng C, Loh T P. Angew Chem Int Ed, 2014, 53: 2722
|
[58] | Jones W D. Acc Chem Res, 2003, 36: 140
|
[59] | Cui S L, Zhang Y, Wu Q F. Chem Sci, 2013, 4: 3421
|
[60] | Hu S, Wang D Q, Liu J X, Li X W. Org Biomol Chem, 2013, 11: 2761
|
[61] | Zhang Y, Wu Q F, Cui S L. Chem Sci, 2014, 5: 297
|
[62] | Liang Y J, Yu K, Li B, Xu S S, Song H B, Wang B Q. Chem Commun, 2014, 50: 6130
|
[63] | Li X G, Sun M, Liu K, Jin Q, Liu P N. Chem Commun, 2015, 51: 2380
|
[64] | Yu S J, Liu S, Lan Y, Wan B X, Li X W. J Am Chem Soc, 2015, 137: 1623
|
[65] | Schro?der N, Lied F, Glorius F. J Am Chem Soc, 2015, 137: 1448
|
[66] | Zhao D B, Vásquez-Céspedes S, Glorius F. Angew Chem Int Ed, 2015, 54: 1657
|
[67] | Fatiadi A J. In: Patai S, Rappaport Z eds. Preparation and Synthetic Applications of Cyano Compounds. New York: Wiley, 1983
|
[68] | Grundmann C. In: Falbe J ed. Houben-Weyl: Methoden der organischen Chemie. 4th Ed. Vol. E5. Stuttgart: Thieme, 1985
|
[69] | Larock R C. Comprehensive Organic Transformations. New York: VCH, 1989
|
[70] | Kleemann A, Engel J, Kutscher B. Pharmaceutical Substances: Synthesis, Patents, Applications. 4th Ed. Stuttgart: Thieme, 2001
|
[71] | Smith M B, March J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 6th Ed. Hoboken: Wiley, 2007
|
[72] | Rappoport Z. The Chemistry of the Cyano Group. New York: Interscience, 1970
|
[73] | Larock R C. Comprehensive Organic Transformations. Weinheim: Wiley-VCH, 1999
|
[74] | Kleemann A, Engel J, Kutschner B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications. 4th Ed. Stuttgart: Thieme, New York, 2001
|
[75] | Miller J S, Manson J L. Acc Chem Res, 2001, 34: 563
|
[76] | Anbarasan P, Schareina T, Beller M. Chem Soc Rev, 2011, 40: 5049
|
[77] | Rosenmund K W, Struck E. Ber Chem, 1919, 52B: 1749
|
[78] | Braun J, Manz G. Liebigs Ann Chem, 1931, 488: 111
|
[79] | Lindley J. Tetrahedron, 1984, 40: 1433
|
[80] | Enders D, Shilvock J P. Chem Soc Rev, 2000, 29: 359
|
[81] | Kuo C W, Zhu J L, Wu J D, Chu C M, Yao C F, Shia K S. Chem Com-mun, 2007: 301
|
[82] | Qin C, Jiao N. J Am Chem Soc, 2010, 132: 15893
|
[83] | Anbarasan P, Neumann H, Beller M. Chem Eur J, 2011, 17: 4217
|
[84] | Wang R, Falck J R. Chem Commun, 2013, 49: 6516
|
[85] | Pawar A B, Chang S. Org Lett, 2015, 17: 660
|
[86] | Ellis G P, Romney-Alexander T M. Chem Rev, 1987, 87: 779
|
[87] | Yang Y, Buchwald S L. Angew Chem Int Ed, 2014, 53: 8677
|
[88] | Xu L, Mou X Q, Chen Z M, Wang S H. Chem Commun, 2014, 50: 10676
|
[89] | Yan Y P, Yuan Y Z, Jiao N. Org Chem Front, 2014, 1: 1176
|
[90] | Zhang L P, Lu P, Wang Y G. Chem Commun, 2015, 51: 2840
|
[91] | Gong T J, Xiao B, Cheng W M, Su W, Xu J, Liu Z J, Liu L, Fu Y. J Am Chem Soc, 2013, 135: 10630
|
[92] | Chaitanya M, Yadagiri D, Anbarasan P. Org Lett, 2013, 15: 4960
|
[93] | Chaitanya M, Anbarasan P. J Org Chem, 2015, 80: 3695
|
[94] | Gu L J, Jin C, Wang R, Ding H Y. ChemCatChem, 2014, 6: 1225
|
[95] | Han J, Pan C D, Jia X F, Zhu C J. Org Biomol Chem, 2014, 12: 8603
|
[96] | Hong X H, Wang H, Qian G Y, Tan Q T, Xu B. J Org Chem, 2014, 79: 3228
|
[97] | Lewis J C, Bergman R G, Ellman J A. Acc Chem Res, 2008, 41: 1013
|
[98] | Satoh T, Miura M. Chem Eur J, 2010, 16: 11212
|
[99] | Wencel-Delord J, Dr?ge T, Liu F, Glorius F. Chem Soc Rev, 2011, 40: 4740
|
[100] | Patureau F W, Wencel-Delord J, Glorius F. Aldrichimica Acta, 2012, 45: 31
|
[101] | Kuhl N, Hopkinson M N, Wencel-Delord J, Glorius F. Angew Chem Int Ed, 2012, 51: 10236
|
[102] | Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41: 3651
|
[103] | Colby D A, Tsai A S, Bergman R G, Ellman J A. Acc Chem Res, 2012, 45: 814
|
[104] | Etayo P, Vidal-Ferran A. Chem Soc Rev, 2013, 42: 728
|
[105] | Karthikeyan J, Cheng C H. Angew Chem Int Ed, 2011, 50: 9880
|
[106] | Wrigglesworth J W, Cox B, Lloyd-Jones G C, Booker-Milburn K I. Org Lett, 2011, 13: 5326
|
[107] | Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc, 2011, 133: 2350
|
[108] | Guimond N, Gorelsky S I, Fagnou K. J Am Chem Soc, 2011, 133: 6449
|
[109] | Wang H G, Glorius F. Angew Chem Int Ed, 2012, 51: 7318
|
[110] | Zeng R, Fu C L, Ma S M. J Am Chem Soc, 2012, 134: 9597
|
[111] | Zeng R, Wu S Z, Fu C L, Ma S M. J Am Chem Soc, 2013, 135: 18284
|
[112] | Yang F Z, Ackermann L. J Org Chem, 2014, 79: 12070
|
[113] | Yang W, Sun J Q, Xu X X, Zhang Q, Liu Q. Chem Commun, 2014, 50: 4420
|
[114] | Liu Y J, Xu H, Kong W J, Shang M, Dai H X, Yu J Q. Nature, 2014, 515: 389
|
[115] | Yu D G, de Azambuja F, Glorius F. Angew Chem Int Ed, 2014, 53: 2754
|
[116] | Yang W, Wang S, Zhang Q, Liu Q, Xu X X. Chem Commun, 2015, 51: 661
|
[117] | Feng C, Loh T P. Angew Chem Int Ed, 2014, 53: 2722
|
[118] | Jones W D. Acc Chem Res, 2003, 36: 140
|
[119] | Cui S L, Zhang Y, Wu Q F. Chem Sci, 2013, 4: 3421
|
[120] | Hu S, Wang D Q, Liu J X, Li X W. Org Biomol Chem, 2013, 11: 2761
|
[121] | Zhang Y, Wu Q F, Cui S L. Chem Sci, 2014, 5: 297
|
[122] | Liang Y J, Yu K, Li B, Xu S S, Song H B, Wang B Q. Chem Commun, 2014, 50: 6130
|
[123] | Li X G, Sun M, Liu K, Jin Q, Liu P N. Chem Commun, 2015, 51: 2380
|
[124] | Yu S J, Liu S, Lan Y, Wan B X, Li X W. J Am Chem Soc, 2015, 137: 1623
|
[125] | Schro?der N, Lied F, Glorius F. J Am Chem Soc, 2015, 137: 1448
|
[126] | Zhao D B, Vásquez-Céspedes S, Glorius F. Angew Chem Int Ed, 2015, 54: 1657
|
[127] | Zhen W C, Du Z G, Li X W. Chin J Catal (甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34: 679
|
[128] | Zhang Y M, Zhang T, Zhan H Q, Li X W. Chin J Catal (张亦猛, 张涛, 詹豪强, 李兴伟. 催化学报), 2014, 35: 1840
|
[129] | Fatiadi A J. In: Patai S, Rappaport Z eds. Preparation and Synthetic Applications of Cyano Compounds. New York: Wiley, 1983
|
[130] | Grundmann C. In: Falbe J ed. Houben-Weyl: Methoden der organischen Chemie. 4th Ed. Vol. E5. Stuttgart: Thieme, 1985
|
[131] | Larock R C. Comprehensive Organic Transformations. New York: VCH, 1989
|
[132] | Kleemann A, Engel J, Kutscher B. Pharmaceutical Substances: Synthesis, Patents, Applications. 4th Ed. Stuttgart: Thieme, 2001
|
[133] | Smith M B, March J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 6th Ed. Hoboken: Wiley, 2007
|
[134] | Rappoport Z. The Chemistry of the Cyano Group. New York: Interscience, 1970
|
[135] | Larock R C. Comprehensive Organic Transformations. Weinheim: Wiley-VCH, 1999
|
[136] | Kleemann A, Engel J, Kutschner B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications. 4th Ed. Stuttgart: Thieme, New York, 2001
|
[137] | Miller J S, Manson J L. Acc Chem Res, 2001, 34: 563
|
[138] | Anbarasan P, Schareina T, Beller M. Chem Soc Rev, 2011, 40: 5049
|
[139] | Rosenmund K W, Struck E. Ber Chem, 1919, 52B: 1749
|
[140] | Braun J, Manz G. Liebigs Ann Chem, 1931, 488: 111
|
[141] | Lindley J. Tetrahedron, 1984, 40: 1433
|
[142] | Enders D, Shilvock J P. Chem Soc Rev, 2000, 29: 359
|
[143] | Kuo C W, Zhu J L, Wu J D, Chu C M, Yao C F, Shia K S. Chem Com-mun, 2007: 301
|
[144] | Qin C, Jiao N. J Am Chem Soc, 2010, 132: 15893
|
[145] | Kobayashi Y, Kamisaki H, Yanada R, Takemoto Y. Org Lett, 2006, 8: 2711
|
[146] | Arai S, Sato T, Koike Y, Hayashi M, Nishida A. Angew Chem Int Ed, 2009, 48: 4528
|
[147] | Arai S, Sato T, Nishida A. Adv Synth Catal, 2009, 351: 1897
|
[148] | Ding S T, Jiao N. J Am Chem Soc, 2011, 133: 12374
|
[149] | Sawant D N, Wagh Y S, Tambade P J, Bhatte K D, Bhanage B M. Adv Synth Catal, 2011, 353: 781
|
[150] | Wen Q D, Jin J S, Hu B B, Lu P, Wang Y. RSC Adv, 2012, 2: 6167
|
[151] | Yang C T, Han J, Liu J, Gu M, Li Y, Wen J, Yu H Z, Hu S, Wang X L. Org Biomol Chem, 2015, 13: 2541
|
[152] | Kou X Z, Zhao M D, Qiao X X, Zhu Y M, Tong X F, Shen Z M. Chem Eur J, 2013, 19: 16880
|
[153] | Pan C D, Jin H M, Xu P, Liu X, Cheng Y X, Zhu C J. J Org Chem, 2013, 78: 9494
|
[154] | Xu H, Liu P T, Li Y H, Han F S. Org Lett, 2013, 15: 3354
|
[155] | Yang Y, Buchwald S L. Angew Chem Int Ed, 2014, 53: 8677
|
[156] | Xu L, Mou X Q, Chen Z M, Wang S H. Chem Commun, 2014, 50: 10676
|
[157] | Chaitanya M, Yadagiri D, Anbarasan P. Org Lett, 2013, 15: 4960
|
[158] | Chaitanya M, Anbarasan P. J Org Chem, 2015, 80: 3695
|
[159] | Gu L J, Jin C, Wang R, Ding H Y. ChemCatChem, 2014, 6: 1225
|
[160] | Han J, Pan C D, Jia X F, Zhu C J. Org Biomol Chem, 2014, 12: 8603
|
[161] | Hong X H, Wang H, Qian G Y, Tan Q T, Xu B. J Org Chem, 2014, 79: 3228
|
[162] | Lewis J C, Bergman R G, Ellman J A. Acc Chem Res, 2008, 41: 1013
|
[163] | Satoh T, Miura M. Chem Eur J, 2010, 16: 11212
|
[164] | Wencel-Delord J, Dr?ge T, Liu F, Glorius F. Chem Soc Rev, 2011, 40: 4740
|
[165] | Patureau F W, Wencel-Delord J, Glorius F. Aldrichimica Acta, 2012, 45: 31
|
[166] | Kuhl N, Hopkinson M N, Wencel-Delord J, Glorius F. Angew Chem Int Ed, 2012, 51: 10236
|
[167] | Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41: 3651
|
[168] | Yan G B, Wu X M, Yang M H. Org Biomol Chem, 2013, 11: 5558
|
[169] | Shi J J, Zhou J, Yan Y N, Jia J L, Liu X L, Song H C, Xu H E, Yi W. Chem Commun, 2015, 51: 668.
|
[170] | Oxgaard J, Tenn W J, Nielsen R J, Periana R A, Goddard W A. Or-ganometallics, 2007, 26: 1565
|
[171] | Ackermann L. Chem Rev, 2011, 111: 1315
|
[172] | Ma W B, Ackermann L. Chem Eur J, 2013, 19: 13925
|
[173] | Ma W B, Mei R H, Tenti G, Ackermann L. Chem Eur J, 2014, 20: 15248
|
[174] | Jia J L, Shi J J, Zhou J, Liu X L, Song Y L, Xu H E, Yi W. Chem Commun, 2015, 51: 2925
|
[175] | Cui S L, Zhang Y, Wu Q F. Chem Sci, 2013, 4: 3421
|
[176] | Hu S, Wang D Q, Liu J X, Li X W. Org Biomol Chem, 2013, 11: 2761
|
[177] | Zhang Y, Wu Q F, Cui S L. Chem Sci, 2014, 5: 297
|
[178] | Liang Y J, Yu K, Li B, Xu S S, Song H B, Wang B Q. Chem Commun, 2014, 50: 6130
|
[179] | Li X G, Sun M, Liu K, Jin Q, Liu P N. Chem Commun, 2015, 51: 2380
|
[180] | Yu S J, Liu S, Lan Y, Wan B X, Li X W. J Am Chem Soc, 2015, 137: 1623
|
[181] | Schro?der N, Lied F, Glorius F. J Am Chem Soc, 2015, 137: 1448
|
[182] | Zhao D B, Vásquez-Céspedes S, Glorius F. Angew Chem Int Ed, 2015, 54: 1657
|
[183] | Zhen W C, Du Z G, Li X W. Chin J Catal (甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34: 679
|
[184] | Zhang Y M, Zhang T, Zhan H Q, Li X W. Chin J Catal (张亦猛, 张涛, 詹豪强, 李兴伟. 催化学报), 2014, 35: 1840
|
[185] | Fatiadi A J. In: Patai S, Rappaport Z eds. Preparation and Synthetic Applications of Cyano Compounds. New York: Wiley, 1983
|
[186] | Grundmann C. In: Falbe J ed. Houben-Weyl: Methoden der organischen Chemie. 4th Ed. Vol. E5. Stuttgart: Thieme, 1985
|
[187] | Larock R C. Comprehensive Organic Transformations. New York: VCH, 1989
|
[188] | Kleemann A, Engel J, Kutscher B. Pharmaceutical Substances: Synthesis, Patents, Applications. 4th Ed. Stuttgart: Thieme, 2001
|
[189] | Smith M B, March J. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 6th Ed. Hoboken: Wiley, 2007
|
[190] | Rappoport Z. The Chemistry of the Cyano Group. New York: Interscience, 1970
|
[191] | Larock R C. Comprehensive Organic Transformations. Weinheim: Wiley-VCH, 1999
|
[192] | Kleemann A, Engel J, Kutschner B, Reichert D. Pharmaceutical Substances: Syntheses, Patents, Applications. 4th Ed. Stuttgart: Thieme, New York, 2001
|
[193] | Miller J S, Manson J L. Acc Chem Res, 2001, 34: 563
|
[194] | Anbarasan P, Schareina T, Beller M. Chem Soc Rev, 2011, 40: 5049
|
[195] | Rosenmund K W, Struck E. Ber Chem, 1919, 52B: 1749
|
[196] | Braun J, Manz G. Liebigs Ann Chem, 1931, 488: 111
|
[197] | Lindley J. Tetrahedron, 1984, 40: 1433
|
[198] | Enders D, Shilvock J P. Chem Soc Rev, 2000, 29: 359
|
[199] | Kuo C W, Zhu J L, Wu J D, Chu C M, Yao C F, Shia K S. Chem Com-mun, 2007: 301
|
[200] | Qin C, Jiao N. J Am Chem Soc, 2010, 132: 15893
|
[201] | Anbarasan P, Neumann H, Beller M. Chem Eur J, 2011, 17: 4217
|
[202] | Wang R, Falck J R. Chem Commun, 2013, 49: 6516
|
[203] | Pawar A B, Chang S. Org Lett, 2015, 17: 660
|
[204] | Ellis G P, Romney-Alexander T M. Chem Rev, 1987, 87: 779
|
[205] | Anbarasan P, Neumann H, Beller M. Angew Chem Int Ed, 2011, 50: 519
|
[206] | Anbarasan P, Neumann H, Beller M. Chem Eur J, 2011, 17: 4217
|
[207] | Kim J, Kim H J, Chang S. Angew Chem Int Ed, 2012, 51: 11948
|
[208] | Senecal T D, Shu W, Buchwald S L. Angew Chem Int Ed, 2013, 52: 10035
|
[209] | Coppola A, Sánchez-Alonso P, Sucunza D, Burgos C, Alajarín R, Alvarez-Builla J, Mosquera M E G, Vaquero J J. Org Lett, 2013, 15: 3388
|
[210] | Liu W, Ackermann L. Chem Commun, 2014, 50: 1878
|
[211] | Yu D G, Gensch T, de Azambuja F, Vásquez-Céspedes S, Glorius F. J Am Chem Soc, 2014, 136: 17722
|
[212] | Li J, Ackermann L. Angew Chem Int Ed, 2015, 54: 3635
|
[213] | Nozaki K, Sato N, Takaya H. J Org Chem, 1994, 59: 2679
|
[214] | Luo F H, Chu C I, Cheng C H. Organometallics, 1998, 17: 1025
|
[215] | Sundermeier M, Zapf A, Beller M. Angew Chem Int Ed, 2003, 42: 1661
|
[216] | Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M. J Organomet Chem, 2003, 684: 50
|
[217] | Kobayashi Y, Kamisaki H, Yanada R, Takemoto Y. Org Lett, 2006, 8: 2711
|
[218] | Arai S, Sato T, Koike Y, Hayashi M, Nishida A. Angew Chem Int Ed, 2009, 48: 4528
|
[219] | Arai S, Sato T, Nishida A. Adv Synth Catal, 2009, 351: 1897
|
[220] | Ding S T, Jiao N. J Am Chem Soc, 2011, 133: 12374
|
[221] | Sawant D N, Wagh Y S, Tambade P J, Bhatte K D, Bhanage B M. Adv Synth Catal, 2011, 353: 781
|
[222] | Wen Q D, Jin J S, Hu B B, Lu P, Wang Y. RSC Adv, 2012, 2: 6167
|
[223] | Yang C T, Han J, Liu J, Gu M, Li Y, Wen J, Yu H Z, Hu S, Wang X L. Org Biomol Chem, 2015, 13: 2541
|
[224] | Zhang L P, Lu P, Wang Y G. Chem Commun, 2015, 51: 2840
|
[225] | Wencel-Delord J, Dr?ge T, Liu F, Glorius F. Chem Soc Rev, 2011, 40: 4740
|
[226] | Patureau F W, Wencel-Delord J, Glorius F. Aldrichimica Acta, 2012, 45: 31
|
[227] | Kuhl N, Hopkinson M N, Wencel-Delord J, Glorius F. Angew Chem Int Ed, 2012, 51: 10236
|
[228] | Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41: 3651
|
[229] | Colby D A, Tsai A S, Bergman R G, Ellman J A. Acc Chem Res, 2012, 45: 814
|
[230] | Etayo P, Vidal-Ferran A. Chem Soc Rev, 2013, 42: 728
|
[231] | Yan G B, Wu X M, Yang M H. Org Biomol Chem, 2013, 11: 5558
|
[232] | Kuhl N, Schr?der N. Glorius F. Adv Synth Catal, 2014, 356: 1443
|
[233] | Zhang M, Zhang Y F, Jie X M, Zhao H Q, Li G, Su W P. Org Chem Front, 2014, 1: 843
|
[234] | Zhen W C, Du Z G, Li X W. Chin J Catal (甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34: 679
|
[235] | Zhang Y M, Zhang T, Zhan H Q, Li X W. Chin J Catal (张亦猛, 张涛, 詹豪强, 李兴伟. 催化学报), 2014, 35: 1840
|
[236] | Anbarasan P, Neumann H, Beller M. Angew Chem Int Ed, 2011, 50: 519
|
[237] | Anbarasan P, Neumann H, Beller M. Chem Eur J, 2011, 17: 4217
|
[238] | Kim J, Kim H J, Chang S. Angew Chem Int Ed, 2012, 51: 11948
|
[239] | Senecal T D, Shu W, Buchwald S L. Angew Chem Int Ed, 2013, 52: 10035
|
[240] | Coppola A, Sánchez-Alonso P, Sucunza D, Burgos C, Alajarín R, Alvarez-Builla J, Mosquera M E G, Vaquero J J. Org Lett, 2013, 15: 3388
|
[241] | Liu W, Ackermann L. Chem Commun, 2014, 50: 1878
|
[242] | Yu D G, Gensch T, de Azambuja F, Vásquez-Céspedes S, Glorius F. J Am Chem Soc, 2014, 136: 17722
|
[243] | Li J, Ackermann L. Angew Chem Int Ed, 2015, 54: 3635
|
[244] | Nozaki K, Sato N, Takaya H. J Org Chem, 1994, 59: 2679
|
[245] | Luo F H, Chu C I, Cheng C H. Organometallics, 1998, 17: 1025
|
[246] | Sundermeier M, Zapf A, Beller M. Angew Chem Int Ed, 2003, 42: 1661
|
[247] | Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M. J Organomet Chem, 2003, 684: 50
|
[248] | Kobayashi Y, Kamisaki H, Yanada R, Takemoto Y. Org Lett, 2006, 8: 2711
|
[249] | Arai S, Sato T, Koike Y, Hayashi M, Nishida A. Angew Chem Int Ed, 2009, 48: 4528
|
[250] | Arai S, Sato T, Nishida A. Adv Synth Catal, 2009, 351: 1897
|
[251] | Ding S T, Jiao N. J Am Chem Soc, 2011, 133: 12374
|
[252] | Sawant D N, Wagh Y S, Tambade P J, Bhatte K D, Bhanage B M. Adv Synth Catal, 2011, 353: 781
|
[253] | Wen Q D, Jin J S, Hu B B, Lu P, Wang Y. RSC Adv, 2012, 2: 6167
|
[254] | Yang C T, Han J, Liu J, Gu M, Li Y, Wen J, Yu H Z, Hu S, Wang X L. Org Biomol Chem, 2015, 13: 2541
|
[255] | Kou X Z, Zhao M D, Qiao X X, Zhu Y M, Tong X F, Shen Z M. Chem Eur J, 2013, 19: 16880
|
[256] | Pan C D, Jin H M, Xu P, Liu X, Cheng Y X, Zhu C J. J Org Chem, 2013, 78: 9494
|
[257] | Xu H, Liu P T, Li Y H, Han F S. Org Lett, 2013, 15: 3354
|
[258] | Yan G B, Wu X M, Yang M H. Org Biomol Chem, 2013, 11: 5558
|
[259] | Kuhl N, Schr?der N. Glorius F. Adv Synth Catal, 2014, 356: 1443
|
[260] | Zhang M, Zhang Y F, Jie X M, Zhao H Q, Li G, Su W P. Org Chem Front, 2014, 1: 843
|
[261] | Han Y F, Jin G X. Chem Soc Rev, 2014, 43: 2799
|
[262] | He R, Huang Z T, Zheng Q Y, Wang C. Tetrahedron Lett, 2014, 55: 5705
|
[263] | Song G Y, Li X W. Acc Chem Res, 2015, 48: 1007
|
[264] | Wang D H, Wasa M, Giri R, Yu J Q. J Am Chem Soc, 2008, 130: 7190
|
[265] | Wasa M, Yu J Q. J Am Chem Soc, 2008, 130: 14058
|
[266] | Guimond N, Gouliaras C, Fagnou K. J Am Chem Soc, 2010, 132: 6908
|
[267] | Wang G W, Yuan T T. J Org Chem, 2010, 75: 476
|
[268] | Shi J J, Zhou J, Yan Y N, Jia J L, Liu X L, Song H C, Xu H E, Yi W. Chem Commun, 2015, 51: 668.
|
[269] | Oxgaard J, Tenn W J, Nielsen R J, Periana R A, Goddard W A. Or-ganometallics, 2007, 26: 1565
|
[270] | Ackermann L. Chem Rev, 2011, 111: 1315
|
[271] | Ma W B, Ackermann L. Chem Eur J, 2013, 19: 13925
|
[272] | Ma W B, Mei R H, Tenti G, Ackermann L. Chem Eur J, 2014, 20: 15248
|
[273] | Jia J L, Shi J J, Zhou J, Liu X L, Song Y L, Xu H E, Yi W. Chem Commun, 2015, 51: 2925
|
[274] | Ackermann L, Lygin A V. Org Lett, 2012, 14: 764
|
[275] | Ackermann L, Wang L H, Wolfram R, Lygin A V. Org Lett, 2012, 14: 728
|
[276] | Qi Z S, Wang M, Li X W. Chem Commun, 2014, 50: 9776
|
[277] | Duan P P, Lan X, Chen Y, Qian S S, Li J J, Lu L, Lu Y B, Chen B, Hong M, Zhao J. Chem Commun, 2014, 50: 12135
|
[278] | Shen Y Y, Liu G X, Zhou Z, Lu X Y. Org Lett, 2013, 15: 3366
|
[279] | Zhou J, Shi J J, Liu X L, Jia J L, Song H C, Xu H E, Yi W. Chem Commun, 2015, 51: 5868
|
[280] | Qi Z S, Li X W. Chin J Catal (戚自松, 李兴伟. 催化学报), 2015, 36: 48
|
[281] | Simmons E M, Hartwig J F. Angew Chem Int Ed, 2012, 51: 3066
|
[282] | Anbarasan P, Neumann H, Beller M. Chem Eur J, 2011, 17: 4217
|
[283] | Wang R, Falck J R. Chem Commun, 2013, 49: 6516
|
[284] | Pawar A B, Chang S. Org Lett, 2015, 17: 660
|
[285] | Ellis G P, Romney-Alexander T M. Chem Rev, 1987, 87: 779
|
[286] | Anbarasan P, Neumann H, Beller M. Angew Chem Int Ed, 2011, 50: 519
|
[287] | Anbarasan P, Neumann H, Beller M. Chem Eur J, 2011, 17: 4217
|
[288] | Kim J, Kim H J, Chang S. Angew Chem Int Ed, 2012, 51: 11948
|
[289] | Senecal T D, Shu W, Buchwald S L. Angew Chem Int Ed, 2013, 52: 10035
|
[290] | Coppola A, Sánchez-Alonso P, Sucunza D, Burgos C, Alajarín R, Alvarez-Builla J, Mosquera M E G, Vaquero J J. Org Lett, 2013, 15: 3388
|
[291] | Liu W, Ackermann L. Chem Commun, 2014, 50: 1878
|
[292] | Yu D G, Gensch T, de Azambuja F, Vásquez-Céspedes S, Glorius F. J Am Chem Soc, 2014, 136: 17722
|
[293] | Li J, Ackermann L. Angew Chem Int Ed, 2015, 54: 3635
|
[294] | Nozaki K, Sato N, Takaya H. J Org Chem, 1994, 59: 2679
|
[295] | Luo F H, Chu C I, Cheng C H. Organometallics, 1998, 17: 1025
|
[296] | Sundermeier M, Zapf A, Beller M. Angew Chem Int Ed, 2003, 42: 1661
|
[297] | Sundermeier M, Mutyala S, Zapf A, Spannenberg A, Beller M. J Organomet Chem, 2003, 684: 50
|
[298] | Yan Y P, Yuan Y Z, Jiao N. Org Chem Front, 2014, 1: 1176
|
[299] | Zhang L P, Lu P, Wang Y G. Chem Commun, 2015, 51: 2840
|
[300] | Gong T J, Xiao B, Cheng W M, Su W, Xu J, Liu Z J, Liu L, Fu Y. J Am Chem Soc, 2013, 135: 10630
|
[301] | Colby D A, Tsai A S, Bergman R G, Ellman J A. Acc Chem Res, 2012, 45: 814
|
[302] | Etayo P, Vidal-Ferran A. Chem Soc Rev, 2013, 42: 728
|
[303] | Kuhl N, Schr?der N. Glorius F. Adv Synth Catal, 2014, 356: 1443
|
[304] | Zhang M, Zhang Y F, Jie X M, Zhao H Q, Li G, Su W P. Org Chem Front, 2014, 1: 843
|
[305] | Han Y F, Jin G X. Chem Soc Rev, 2014, 43: 2799
|
[306] | He R, Huang Z T, Zheng Q Y, Wang C. Tetrahedron Lett, 2014, 55: 5705
|
[307] | Song G Y, Li X W. Acc Chem Res, 2015, 48: 1007
|
[308] | Wang D H, Wasa M, Giri R, Yu J Q. J Am Chem Soc, 2008, 130: 7190
|
[309] | Wasa M, Yu J Q. J Am Chem Soc, 2008, 130: 14058
|
[310] | Guimond N, Gouliaras C, Fagnou K. J Am Chem Soc, 2010, 132: 6908
|
[311] | Wang G W, Yuan T T. J Org Chem, 2010, 75: 476
|
[312] | Karthikeyan J, Cheng C H. Angew Chem Int Ed, 2011, 50: 9880
|
[313] | Wrigglesworth J W, Cox B, Lloyd-Jones G C, Booker-Milburn K I. Org Lett, 2011, 13: 5326
|
[314] | Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc, 2011, 133: 2350
|
[315] | Guimond N, Gorelsky S I, Fagnou K. J Am Chem Soc, 2011, 133: 6449
|
[316] | Wang H G, Glorius F. Angew Chem Int Ed, 2012, 51: 7318
|
[317] | Zeng R, Fu C L, Ma S M. J Am Chem Soc, 2012, 134: 9597
|
[318] | Zeng R, Wu S Z, Fu C L, Ma S M. J Am Chem Soc, 2013, 135: 18284
|
[319] | Yang F Z, Ackermann L. J Org Chem, 2014, 79: 12070
|
[320] | Yang W, Sun J Q, Xu X X, Zhang Q, Liu Q. Chem Commun, 2014, 50: 4420
|
[321] | Liu Y J, Xu H, Kong W J, Shang M, Dai H X, Yu J Q. Nature, 2014, 515: 389
|
[322] | Yu D G, de Azambuja F, Glorius F. Angew Chem Int Ed, 2014, 53: 2754
|
[323] | Yang W, Wang S, Zhang Q, Liu Q, Xu X X. Chem Commun, 2015, 51: 661
|
[324] | Ackermann L, Lygin A V. Org Lett, 2012, 14: 764
|
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