Rhodium-Catalyzed Annulation of 4-Arylbut-3-yn-1-amines with Internal Alkynes through C-H Functionalization.

Org Lett

Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle , Nanchang Hangkong University, Nanchang 330063 , China.

Published: January 2019

A new, one-step rhodium(III)-catalyzed annulation of 4-arylbut-3-yn-1-amines with internal alkynes through C-H functionalization is reported. This reaction allows the formation of three new chemical bonds, including two C-C bonds and one C-N band, thus selectively assembling various spiro[indene-1,2'-pyrrolidine]s with excellent functional group compatibility, high atom-economy, and step-efficiency.

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http://dx.doi.org/10.1021/acs.orglett.8b03561DOI Listing

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In the realm of transition-metal catalyzed arene functionalization, rhodium(III) catalysis is considered as exemplary due to its propensity to activate C-H bonds to obtain comprehensive molecular assembly. Herein, we demonstrate a new rhodium(III) catalyzed assembly of polyheterocyclic scaffolds via C-H activation and regioselective annulation of 4-arylbut-3-yn-1-amines with 4-hydroxy-2-alkynoates. Heterocyclization and trans-metalation prior to annulation is the key for initiation of this relay redox-neutral catalytic cascade.

View Article and Find Full Text PDF

Rhodium-Catalyzed Annulation of 4-Arylbut-3-yn-1-amines with Internal Alkynes through C-H Functionalization.

Org Lett

January 2019

Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle , Nanchang Hangkong University, Nanchang 330063 , China.

A new, one-step rhodium(III)-catalyzed annulation of 4-arylbut-3-yn-1-amines with internal alkynes through C-H functionalization is reported. This reaction allows the formation of three new chemical bonds, including two C-C bonds and one C-N band, thus selectively assembling various spiro[indene-1,2'-pyrrolidine]s with excellent functional group compatibility, high atom-economy, and step-efficiency.

View Article and Find Full Text PDF

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