Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of N-carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence

Organic Letters
Xiao-Fei YangTeck-Peng Loh

Abstract

A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity.

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Citations

Dec 22, 2015·The Journal of Organic Chemistry·Wucheng XieBaiquan Wang
Jul 18, 2015·Journal of the American Chemical Society·Xinyao LiNing Jiao
Apr 26, 2016·Chemical Reviews·Vadim P BoyarskiyAleksander V Vasilyev
May 11, 2016·The Journal of Organic Chemistry·Ya-Nan HuangJun Deng
Jan 19, 2017·Journal of the American Chemical Society·Cheng-Qiang WangTeck-Peng Loh
Jan 14, 2016·Chemical Communications : Chem Comm·Yudong YangJingsong You
Nov 11, 2015·Organic & Biomolecular Chemistry·Shuai-Shuai LiLin Dong
Aug 1, 2015·Organic & Biomolecular Chemistry·Ramasamy Manoharan, Masilamani Jeganmohan
Apr 7, 2016·Chemical Communications : Chem Comm·K DevarajL T Pilarski
May 14, 2016·Organic & Biomolecular Chemistry·Zengqiang Song, Andrey P Antonchick
Dec 15, 2015·Chemical Communications : Chem Comm·Jiaping WuCheng Ma
Oct 30, 2015·Angewandte Chemie·Lanting XuDawei Ma
Feb 1, 2019·Organic & Biomolecular Chemistry·Kangkan TalukdarTharmalingam Punniyamurthy

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