A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

André-Joyaux, Emy; Kuzovlev, Andrey; Tappin, Nicholas D. C.; Renaud, Philippe (2020). A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters. Angewandte Chemie (International ed.), 59(33), pp. 13859-13864. Wiley-VCH 10.1002/anie.202004012

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The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C−C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

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