Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

Shengjin Song; Huan Liu; Lu Wang; Chuan Zhu; Teck Peng Loh; Chao Feng

doi:10.1002/cjoc.201900197

Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

Shengjin Song, Huan Liu, Lu Wang, Chuan Zhu, Teck Peng Loh^*, Chao Feng

^*Corresponding author for this work

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

24 Citations (Scopus)

Abstract

Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp²)—C(sp²) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp²)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.

Original language	English
Pages (from-to)	1036-1040
Number of pages	5
Journal	Chinese Journal of Chemistry
Volume	37
Issue number	10
DOIs	https://doi.org/10.1002/cjoc.201900197
Publication status	Published - Oct 1 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

ASJC Scopus Subject Areas

General Chemistry

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10.1002/cjoc.201900197

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abstract = "Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.",

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T1 - Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

AU - Song, Shengjin

AU - Liu, Huan

AU - Wang, Lu

AU - Zhu, Chuan

AU - Loh, Teck Peng

AU - Feng, Chao

PY - 2019/10/1

Y1 - 2019/10/1

N2 - Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.

AB - Herein, we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)—C(sp2) cross-coupling of gem-difluoroalkenes and acrylamides. By merging Rh(III)-catalyzed C(sp2)–H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene, an efficient defluorinative vinylation reaction is uncovered, which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild conditions. Preliminary mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.

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Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

Abstract

Bibliographical note

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