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Synfacts 2024; 20(12): 1265
DOI: 10.1055/a-2439-7209
Metals in Synthesis

Copper-Catalyzed Cross-Nucleophile Alkylarylation of Vinylarenes with Two Different Boronic Acids

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare 
,
Phillip Pommerening
Lee S, Yu JD, Monterde AL, Tung SE, Wang Y-N, Gay BL, Hull KL. * University of Texas at Austin, USA
Chemoselective Cu-Catalyzed Cross-Nucleophile Alkylarylation of Alkenes.

ACS Catal 2024;
14: 14242-14250
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Keywords

alkenes - alkylarylation - boronic acids - cross-nucleophile coupling - 1,1-diarylalkanes

Significance

Hull and co-workers report an oxidative cross-nucleophile strategy for the alkylarylation of vinyl arenes using two different boronic acids. This operationally simple and scalable protocol provides straightforward access to 1,1-diarylalkanes.


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Comment

Mechanistic investigations support the shown mechanism. Lewis pair formation of the in situ formed boroxines and the added amine was found to be crucial for this transformation (see gray box).


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Publication History

Article published online:
21 November 2024

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