Redox-Neutral Rhodium-Catalyzed [4+1] Annulation through Formal Dehydrogenative Vinylidene Insertion

Huan Liu; Shengjin Song; Cheng Qiang Wang; Chao Feng; Teck Peng Loh

doi:10.1002/cssc.201601341

Redox-Neutral Rhodium-Catalyzed [4+1] Annulation through Formal Dehydrogenative Vinylidene Insertion

Huan Liu, Shengjin Song, Cheng Qiang Wang, Chao Feng^*, Teck Peng Loh

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

50 Citations (Scopus)

Abstract

A synthetic protocol for the expedient construction of 5-methylene-1H-pyrrol-2(5H)-one derivatives through rhodium-catalyzed [4+1] annulation with gem-difluoroacrylate as the C₁component was reported. By taking advantage of the twofold C−F bond cleavage occurring during the annulation, this reaction not only allows the synthesis of these heterocyclic compounds under overall oxidant-free conditions but also renders the transformation stereospecific. The very mild reaction conditions employed ensure compatibility with a wide variety of synthetically useful functional groups.

Original language	English
Pages (from-to)	58-61
Number of pages	4
Journal	ChemSusChem
Volume	10
Issue number	1
DOIs	https://doi.org/10.1002/cssc.201601341
Publication status	Published - Jan 10 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

Environmental Chemistry
General Chemical Engineering
General Materials Science
General Energy

Keywords

amides
annulation
C−H activation
fluoroalkenes
rhodium

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10.1002/cssc.201601341

Cite this

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abstract = "A synthetic protocol for the expedient construction of 5-methylene-1H-pyrrol-2(5H)-one derivatives through rhodium-catalyzed [4+1] annulation with gem-difluoroacrylate as the C1component was reported. By taking advantage of the twofold C−F bond cleavage occurring during the annulation, this reaction not only allows the synthesis of these heterocyclic compounds under overall oxidant-free conditions but also renders the transformation stereospecific. The very mild reaction conditions employed ensure compatibility with a wide variety of synthetically useful functional groups.",

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AU - Loh, Teck Peng

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Redox-Neutral Rhodium-Catalyzed [4+1] Annulation through Formal Dehydrogenative Vinylidene Insertion

Abstract

Bibliographical note

ASJC Scopus Subject Areas

Keywords

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