Chemodivergent Oxidative Annulation of Benzamides and Enynes via 1,4-Rhodium Migration

Organic Letters
Jiaqiong SunXingwei Li

Abstract

Chemodivergent annulative couplings have been realized between N-methoxy benzamides and 1,3-enynes via Rh-catalyzed C-H activation and 1,4-Rh migration. Under Rh/copper catalyzed aerobic conditions, the nitrogen annulation occurred as the major pathway. The chemoselectivity was switched to the oxygen annulation under proper condition control with stoichiometric amounts of Cu(II) oxidant and NaOAc. Both coupling systems proceeded with a broad scope and functional group tolerance.

References

Feb 1, 1996·Chemical Reviews·Barry M. Trost, David L. Van Vranken
Feb 3, 2005·Journal of the American Chemical Society·Tomoya MiuraMasahiro Murakami
Nov 8, 2005·Angewandte Chemie·Shengming Ma, Zhenhua Gu
Oct 2, 2008·Journal of the American Chemical Society·Barry M Trost, David A Thaisrivongs
Aug 27, 2010·Chemistry : a European Journal·Tetsuya Satoh, Masahiro Miura
Feb 5, 2011·Angewandte Chemie·Frederic W Patureau, Frank Glorius
Jan 1, 2010·Topics in Current Chemistry·Feng Shi, Richard C Larock
Sep 10, 2011·The Journal of Organic Chemistry·Dan ChenXingwei Li
Dec 14, 2011·Accounts of Chemical Research·Denise A ColbyJonathan A Ellman
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Mar 2, 2012·Chemical Society Reviews·Guoyong SongXingwei Li
May 5, 2012·Accounts of Chemical Research·Sharon R Neufeldt, Melanie S Sanford
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Sep 22, 2012·Angewandte Chemie·Nadine KuhlFrank Glorius
May 21, 2014·Angewandte Chemie·Benjamin M PartridgeHon Wai Lam
May 23, 2014·Journal of the American Chemical Society·Ryo ShintaniKyoko Nozaki
Jul 2, 2014·Chemical Society Reviews·Fengzhi Zhang, David R Spring
Oct 23, 2014·Journal of the American Chemical Society·Yuki FukuiGuo-Qiang Lin
Nov 25, 2014·Chemical Society Reviews·Huawen HuangHuanfeng Jiang
Apr 7, 2015·Accounts of Chemical Research·Guoyong Song, Xingwei Li
Apr 18, 2015·Accounts of Chemical Research·Baihua Ye, Nicolai Cramer
Jul 18, 2015·Chemical Society Reviews·Zhongxing HuangGuangbin Dong
Jan 14, 2016·Chemical Communications : Chem Comm·Yudong YangJingsong You
Apr 14, 2016·Chemical Society Reviews·T GenschJ Wencel-Delord
Jun 23, 2016·Accounts of Chemical Research·Nicola Della Ca'Marta Catellani
Aug 2, 2016·Angewandte Chemie·Ru-Yi ZhuJin-Quan Yu
Aug 23, 2016·Journal of the American Chemical Society·Stamatis E KorkisHon Wai Lam
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Jan 14, 2017·Chemical Reviews·Yudong YangJingsong You
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong

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Citations

Sep 15, 2020·Chemical Society Reviews·Irina P BeletskayaMiguel Yus

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