A Radical FLP Approach to C–C Coupling

Michael S. Hill

doi:10.1016/j.chempr.2020.02.008

A Radical FLP Approach to C–C Coupling

Michael S. Hill

Department of Chemistry

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Abstract

In the February issue of Cell Reports Physical Science, Melen and co-workers report the reactivity of diaryl-substituted esters with R₃P/B(C₆F₅)₃ frustrated Lewis pairs (FLPs). Although ester C–O activation occurs for all FLP systems, the use of Mes₃P induces single-electron transfer to generate a [Mes₃P]^⋅+/[C(H)Ar₂]^⋅ radical ion pair. In the presence of olefins, this reactivity is harnessed in an sp²-sp³ C–C heterocoupling reaction to generate α,β-substituted olefins.

Original language	English
Pages (from-to)	550-551
Number of pages	2
Journal	Chem
Volume	6
Issue number	3
Early online date	27 Feb 2020
DOIs	https://doi.org/10.1016/j.chempr.2020.02.008
Publication status	Published - 12 Mar 2020

ASJC Scopus subject areas

General Chemistry
Biochemistry
Environmental Chemistry
General Chemical Engineering
Biochemistry, medical
Materials Chemistry

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10.1016/j.chempr.2020.02.008

Melen_Cell Reports_prview_acceptedAccepted author manuscript, 302 KBLicence: CC BY-NC-ND

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title = "A Radical FLP Approach to C–C Coupling",

abstract = "In the February issue of Cell Reports Physical Science, Melen and co-workers report the reactivity of diaryl-substituted esters with R3P/B(C6F5)3 frustrated Lewis pairs (FLPs). Although ester C–O activation occurs for all FLP systems, the use of Mes3P induces single-electron transfer to generate a [Mes3P]⋅+/[C(H)Ar2]⋅ radical ion pair. In the presence of olefins, this reactivity is harnessed in an sp2-sp3 C–C heterocoupling reaction to generate α,β-substituted olefins.",

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AB - In the February issue of Cell Reports Physical Science, Melen and co-workers report the reactivity of diaryl-substituted esters with R3P/B(C6F5)3 frustrated Lewis pairs (FLPs). Although ester C–O activation occurs for all FLP systems, the use of Mes3P induces single-electron transfer to generate a [Mes3P]⋅+/[C(H)Ar2]⋅ radical ion pair. In the presence of olefins, this reactivity is harnessed in an sp2-sp3 C–C heterocoupling reaction to generate α,β-substituted olefins.

UR - https://www.scopus.com/pages/publications/85080995143

U2 - 10.1016/j.chempr.2020.02.008

DO - 10.1016/j.chempr.2020.02.008

M3 - Article

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JO - Chem

JF - Chem

IS - 3

ER -

A Radical FLP Approach to C–C Coupling

Abstract

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