SangHyun Lee, Jianyang D. Yu, Alex L. Monterde, Sarah E. Tung, Ya-Nong Wang, Brittany L. Gay, Kami L. Hull
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引用次数: 0
Abstract
We report a general cross-nucleophile alkene alkylarylation that adds two different boronic acids, an alkyl and an aryl, across a vinylarene to afford 1,1-diarylalkanes. The high chemoselectivity originates from the distinct reactivities of the two boronic acids: the alkylboronic acid is selectively oxidized to an alkyl radical, while the arylboronic acid favors transmetalation with the Cu(II) catalyst. Mechanistic studies suggest that Lewis acid–Lewis base interactions between in situ generated boroxines and added amine are critical for selectivity. A scope of 37 examples is presented with structurally and electronically diverse alkyl, vinyl, and aryl coupling partners. The synthetic utility is demonstrated in the preparation of pimozide and anticancer agent analogues.
期刊介绍：
ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels.
The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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