Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3 –Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)­alk...

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Bibliographic Details
Published in:Organic letters Vol. 18; no. 4; pp. 764 - 767
Main Authors: Patel, Niki R, Kelly, Christopher B, Jouffroy, Matthieu, Molander, Gary A
Format: Journal Article
Language:English
Published: United States American Chemical Society 19-02-2016
Subjects:
Catalysis
Hydrocarbons, Halogenated - chemistry
Letter
Molecular Structure
Nickel - chemistry
Oxidation-Reduction
Photochemical Processes
Silicates - chemistry
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Summary:Single-electron transmetalation via photoredox/nickel dual catalysis provides the opportunity for the construction of Csp3 –Csp2 bonds through the transfer of alkyl radicals under very mild reaction conditions. A general procedure for the cross-coupling of primary and secondary (bis-catecholato)­alkyl­silicates with alkenyl halides is presented. The developed method allows not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides to be employed.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00024