Carbonyl-assisted reverse regioselective cascade annulation of 2-acetylenic ketones triggered by Ru-catalyzed C-H activation

Chemical Science
Krishna Kumar GollapelliRambabu Chegondi

Abstract

The first reverse regioselective intermolecular annulation of aryl substituted 2-acetylenic ketones with O-substituted N-hydroxybenzamides or acrylamides followed by tandem cyclization via ruthenium-catalyzed C-H activation, is reported. Excellent reverse selectivity of alkyne insertion was induced by the weak coordination between the carbonyl group and ruthenium complex. This highly efficient and practical reaction has a broad range of substrate scope with excellent functional-group tolerance. The tandem reaction provides a wide range of polycyclic products that have an indozilidine structural motif, and are found to potentially be synthetically and pharmaceutically valuable.

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Citations

Oct 13, 2018·Organic & Biomolecular Chemistry·Sandip B JadhavRambabu Chegondi
May 23, 2019·Chemistry : a European Journal·Rajagopal Santhoshkumar, Chien-Hong Cheng
Aug 2, 2016·Angewandte Chemie·Ru-Yi ZhuJin-Quan Yu
Sep 29, 2017·Chemical Communications : Chem Comm·Liangliang SongErik V Van der Eycken
Apr 10, 2020·Chemical Communications : Chem Comm·Yating ZhaoWujiong Xia
Aug 23, 2019·Chemical Communications : Chem Comm·Bingxian LiuXingwei Li
Apr 26, 2017·Chemistry : a European Journal·Elena A GinerMiguel A Sierra
Jun 13, 2020·Chemistry : a European Journal·Erik Van der Eycken, Liangliang Song
Jun 13, 2017·The Journal of Organic Chemistry·Raghunath Reddy Anugu, Rambabu Chegondi
Aug 17, 2021·Chemical Communications : Chem Comm·Bhargav DesaiTogati Naveen
Oct 23, 2018·Organic Letters·Rui SunHua Chen
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Nov 9, 2019·The Journal of Organic Chemistry·Ashok DonthojuRambabu Chegondi
Sep 18, 2020·The Journal of Organic Chemistry·Zi YangXiuling Cui
Sep 8, 2021·Organic & Biomolecular Chemistry·Prasanjit Ghosh, Sajal Das

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Methods Mentioned

BETA
NMR
X-ray
column chromatography

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