全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
催化学报  2015 

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

Full-Text   Cite this paper   Add to My Lib

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

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133