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. 2015 Feb 18;137(6):2195-8.
doi: 10.1021/ja512946e. Epub 2015 Feb 4.

Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling

David N Primer  1 , Idris Karakaya, John C Tellis, Gary A Molander
Affiliations

Single-electron transmetalation: an enabling technology for secondary alkylboron cross-coupling

David N Primer et al. J Am Chem Soc. .

Abstract

Single-electron-mediated alkyl transfer affords a novel mechanism for transmetalation, enabling cross-coupling under mild conditions. Here, general conditions are reported for cross-coupling of secondary alkyltrifluoroborates with an array of aryl bromides mediated by an Ir photoredox catalyst and a Ni cross-coupling catalyst.

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Figures

Figure 1
Figure 1
General catalytic cycle for secondary alkyl cross-coupling, depicting side reactions and off-cycle intermediates that may occur.
Figure 2
Figure 2
Comparison between traditional transmetalation and single-electron-mediated activation, and proposed catalytic cycle for photo-redox cross-coupling.
See this image and copyright information in PMC

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