Phosphine-boryl radicals remain less well-studied because their parent phosphine-boranes are highly stable under oxidative conditions. Herein, we report a strategy for generating phosphine-boryl radicals facilitated by radical precursors through an appropriate molecular design. Incorporating a proximal oxidant into a phosphine-borane facilitates the formation of the corresponding boron-centered radical through proton-coupled intramolecular electron transfer. The resulting phosphine-boryl radical can be used to generate an alkyl radical via halogen atom transfer.
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Yu Matsuda
Takahito Kuribara
Tetsuhiro Nemoto
Organic Letters
Chiba University
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Matsuda et al. (Fri,) studied this question.
www.synapsesocial.com/papers/69eefcf4fede9185760d3b82 — DOI: https://doi.org/10.1021/acs.orglett.6c01460