三价铑催化硝酮与炔的碳氢活化偶联合成二氢吲哚

doi:10.1016/S1872-2067(15)60866-X

催化学报 ›› 2015, Vol. 36 ›› Issue (7): 925-932.DOI: 10.1016/S1872-2067(15)60866-X

三价铑催化硝酮与炔的碳氢活化偶联合成二氢吲哚

孔令恒, 谢芳, 于松杰, 戚自松, 李兴伟

中国科学院大连化学物理研究所, 辽宁大连116023

收稿日期:2015-04-22 修回日期:2015-04-30 出版日期:2015-06-12 发布日期:2015-07-30
通讯作者: 李兴伟电话: (0411)84379089; 电子信箱: xwli@dicp.ac.cn
基金资助:
中国科学院大连化学物理研究所; 国家自然科学基金(21272231, 21472186, 21372266).

Rh(III)-catalyzed coupling of nitrones with alkynes for the synthesis of indolines

Lingheng Kong, Fang Xie, Songjie Yu, Zisong Qi, Xingwei Li

Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2015-04-22 Revised:2015-04-30 Online:2015-06-12 Published:2015-07-30
Supported by:
This work was supported by the Dalian Institute of Chemical Physics, Chinese Academy of Sciences, and the National Natural Science Foundation of China (21272231, 21472186, 21372266).

摘要/Abstract

摘要：

三价铑在氧化还原中性条件下催化硝酮与炔发生偶联, 经过氮芳环的碳氢键活化和氧转移可以高化学选择性、中等到良好非对映选择性的得到三取代二氢吲哚.

关键词: 三价铑, 碳氢活化, 氧转移, 氮芳基硝酮

Abstract:

Rh-catalyzed redox-neutral coupling between N-aryl nitrones and alkynes has been achieved under relatively mild conditions. The reaction proceeded via C-H activation at the N-aryl ring with subsequent O-atom transfer, affording trisubstituted indolines in good chemoselectivity and moderate to good diasteroselectivity.

Key words: Rhodium(III), Carbon-hydrogen activation, Oxygen-atom transfer, Nitrogen-aryl nitrones

孔令恒, 谢芳, 于松杰, 戚自松, 李兴伟. 三价铑催化硝酮与炔的碳氢活化偶联合成二氢吲哚[J]. 催化学报, 2015, 36(7): 925-932.

Lingheng Kong, Fang Xie, Songjie Yu, Zisong Qi, Xingwei Li. Rh(III)-catalyzed coupling of nitrones with alkynes for the synthesis of indolines[J]. Chinese Journal of Catalysis, 2015, 36(7): 925-932.

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https://www.cjcatal.com/CN/Y2015/V36/I7/925

参考文献

[1] Chen X, Engle K M, Wang D H, Yu J Q. Angew Chem Int Ed, 2009, 48: 5094
[2] Yeung C S, Dong V M. Chem Rev, 2011, 111: 1215
[3] Wencel-Delord J, Droege T, Liu F, Glorius F. Chem Soc Rev, 2011, 40: 4740
[4] Sun C L, Li B J, Shi Z J. Chem Rev, 2011, 111: 1293
[5] Yamaguchi J, Yamaguchi A D, Itami K. Angew Chem Int Ed, 2012, 51: 8960
[6] McMurray L, O'Hara F, Gaunt M J. Chem Soc Rev, 2011, 40: 1885
[7] Cho S H, Kim J Y, Kwak J, Chang S. Chem Soc Rev, 2011, 40: 5068
[8] Ackermann L. Acc Chem Res, 2014, 47: 281
[9] Ackermann L. Chem Rev, 2011, 111: 1315
[10] Xie F, Qi Z S, Yu S J, Li X W. J Am Chem Soc, 2014, 136: 4780
[11] Kim J Y, Park S H, Ryu J, Cho S H, Kim S H, Chang S. J Am Chem Soc, 2012, 134: 9110
[12] Zhen W C, Du Z Y, Li X W. Chin J Catal (甄文萃, 杜正银, 李兴伟. 催化学报), 2013, 34: 679
[13] Zhao D, Nimphius C, Lindale M, Glorius F. Org Lett, 2013, 15: 4504
[14] Qi Z S, Li X W. Chin J Catal (戚自松, 李兴伟. 催化学报), 2015, 36: 48
[15] Zhang F, Spring D R. Chem Soc Rev, 2014, 43: 6906
[16] Kuhl N, Schröder N, Glorius F. Adv Synth Catal, 2014, 356: 1443
[17] Colby D A, Tsai A S, Bergman R G, Ellman J A. Acc Chem Res, 2012, 45: 814
[18] Song G Y, Wang F, Li X W. Chem Soc Rev, 2012, 41: 3651
[19] Colby D A, Bergman R G, Ellman J A. Chem Rev, 2010, 110: 624
[20] Guimond N, Gouliaras C, Fagnou K. J Am Chem Soc, 2010, 132: 6908
[21] Guimond N, Gorelsky S I, Fagnou K. J Am Chem Soc, 2011, 133: 6449
[22] Patureau F W, Glorius F. Angew Chem Int Ed, 2011, 50: 1977
[23] Rakshit S, Grohmann C, Besset T, Glorius F. J Am Chem Soc, 2011, 133: 2350
[24] Huang H W, Ji X C, Wu W Q, Jiang H F. Chem Soc Rev, 2015, 44: 1155
[25] Hyster T K, Rovis T. Chem Commun, 2011, 47: 11846
[26] Martin R M, Bergman R G, Ellman J A. J Org Chem, 2012, 77: 2501
[27] Wang H G, Glorius F. Angew Chem Int Ed, 2012, 51: 7318
[28] Neely J M, Rovis T. J Am Chem Soc, 2013, 135: 66
[29] Huckins J R, Bercot E A, Thiel O R, Hwang T L, Bio M M. J Am Chem Soc, 2013, 135: 14492
[30] Zhang X P, Chen D, Zhao M, Zhao J, Jia A Q, Li X W. Adv Synth Catal, 2011, 353: 719
[31] Huang X L, Huang J S, Du C L, Zhang X Y, Song F J, You J S. Angew Chem Int Ed, 2013, 52: 12970
[32] Cui S L, Zhang Y, Wu Q F. Chem Sci, 2013, 4: 3421
[33] Liu G X, Shen Y Y, Zhou Z, Lu X Y. Angew Chem Int Ed, 2013, 52: 6033
[34] Shen Y Y, Liu G X, Zhou Z, Lu X Y. Org Lett, 2013, 15: 3366
[35] Shi J J, Zhao G G, Wang X W, Xu H E, Yi W. Org Biomol Chem, 2014, 12: 6831
[36] Chen Y, Wang D Q, Duan P P, Ben R, Dai L, Shao X R, Hong M, Zhao J, Huang Y. Nat Commun, 2014, 5: 4610
[37] Chuang S C, Gandeepan P, Cheng C H. Org Lett, 2013, 15: 5750
[38] Liu B Q, Song C, Sun C, Zhou S G, Zhu J. J Am Chem Soc, 2013, 135: 16625
[39] Zhao D B, Shi Z Z, Glorius F. Angew Chem Int Ed, 2013, 52: 12426
[40] Zheng L Y, Hua R M, Chemistry, 2014, 20: 2352
[41] Wang C M, Sun H, Fang Y, Huang Y. Angew Chem Int Ed, 2013, 52: 5795
[42] Matsuda T, Tomaru Y. Tetrahedron Lett, 2014, 55: 3302
[43] Huang X C, Yang X H, Song R J, Li J H. J Org Chem, 2014, 79: 1025
[44] Fan Z L, Song S S, Li W, Geng K J, Xu Y J, Miao Z H, Zhang A. Org Lett, 2015, 17: 310
[45] Zhang Q R, Huang J R, Zhang W, Dong L. Org Lett, 2014, 16: 1684
[46] Yu S J, Liu S, Lan Y, Wan B S, Li X W. J Am Chem Soc, 2015, 137: 1623
[47] Zhang X Y, Qi Z S, Li X W. Angew Chem Int Ed, 2014, 53: 10794
[48] Sharma U, Park Y, Chang S. J Org Chem, 2014, 79: 9899
[49] Qi Z S, Wang M, Li X W. Org Lett, 2013, 15: 5440
[50] Wang C X, Wang D P, Yan H, Wang H L, Pan B, Xin X Y, Li X C, Wu F, Wan B S. Angew Chem Int Ed, 2014, 53: 11940
[51] Ren Z, Mo F Y, Dong G B. J Am Chem Soc, 2012, 134: 16991
[52] Mawo R Y, Mustakim S, Young V G, Hoffmann M R, Smoliakova I P. Organometallics, 2007, 26: 1801
[53] Bielsa R, Navarro R, Urriolabeitia E P, Lledós A. Inorg Chem, 2007, 46: 10133
[54] Williams R M, Cox R J. Acc Chem Res, 2003, 36: 127
[55] Zhang D, Song H, Qin Y. Acc Chem Res, 2011, 44: 447
[56] Takano S, Ogasawara K. Alkaloids, 1989, 36: 225
[57] Mio M J, Kopel L C, Braun J B, Gadzikwa T L, Hull K L, Brisbois R G, Markworth C J, Grieco P A. Org Lett, 2002, 4: 3199
[58] Dateer R B, Chang S. J Am Chem Soc, 2015, 137: 4908

三价铑催化硝酮与炔的碳氢活化偶联合成二氢吲哚

Rh(III)-catalyzed coupling of nitrones with alkynes for the synthesis of indolines

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