Photoredox Mediated of gem-Diborylalkenes: A New Reactivity Toward Diverse 1,1-Bisborylalkanes

Chemistry : a European Journal
Ahmad MasarwaAlexander Shames

Abstract

The use of gem -diborylalkenes as radical-reactive groups is explored for the first time. These reactions provide an efficient and general method for the photochemical conversion of gem -diborylalkenes to rapidly access 1,1-bisborylalkanes. This method exploits a novel photoredox decarboxylative radical addition to gem -diborylalkenes to afford α- gem diboryl carbon-centered radicals, which benefit from additional stability by virtue of an interaction with the empty p-orbitals on borons. The reaction offers a highly modular and regioselective approach to γ-amino gem -diborylalkanes. Furthermore, EPR spectroscopy and DFT calculations have provided insight into the radical mechanism underlying the photochemistry reaction and the stability of the bis-metalated radicals, respectively.

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Citations

Apr 15, 2021·Journal of the American Chemical Society·Nadim EghbariehAhmad Masarwa
May 28, 2021·Organic Letters·Olamide O IdowuDonald A Watson

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