Radical Hydroboration and Hydrosilylation of gem-Difluoroalkenes: Synthesis of α‑Difluorinated Alkylborons and Alkylsilanes

A first example of radical hydroboration and hydrosilylation of gem-difluoroalkenes using ABIN as the radical initiator is described. This protocol features good functional group tolerance, operational simplicity, high atom economy, and easy scale-up, enabling efficient assembly of a wide range of α...

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Published in:Organic letters 2019-10, Vol.21 (20), p.8454-8458
Main Authors: Liu, Xiaozu, Lin, E Emily, Chen, Guojun, Li, Ji-Lin, Liu, Peijun, Wang, Honggen
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Language:English
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cited_by cdi_FETCH-LOGICAL-a345t-adede28049888d36edc091c68b3cbaa8d8734fc23a33e82316c8cadfbce466fe3
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container_issue 20
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container_title Organic letters
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creator Liu, Xiaozu
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Wang, Honggen
description A first example of radical hydroboration and hydrosilylation of gem-difluoroalkenes using ABIN as the radical initiator is described. This protocol features good functional group tolerance, operational simplicity, high atom economy, and easy scale-up, enabling efficient assembly of a wide range of α-difluorinated alkylborons and alkylsilanes in moderate to excellent yields. The synthetic utility of these products is demonstrated by further transformation of the C–B bond and C–Si bond into valuable CF2-containing molecules.
doi_str_mv 10.1021/acs.orglett.9b03218
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title Radical Hydroboration and Hydrosilylation of gem-Difluoroalkenes: Synthesis of α‑Difluorinated Alkylborons and Alkylsilanes
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