A General Approach to Deboronative Radical Chain Reaction with Pinacol Alkylboronic Estersстатья
Статья опубликована в высокорейтинговом журнале
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Дата последнего поиска статьи во внешних источниках: 12 августа 2020 г.
Аннотация:The generation of carbon-centered radicals from air-
sensitive organoboron compounds via nucleohomolytic substitution at
boron is one of the most general methods to generate non-
functionalized and functionalized radicals. Due to their reduced Lewis
acidity, the very popular, air-stable, and readily available alkylboronic
pinacol esters are not suitable substrates for this process. Herein, is
reported their in situ conversion to alkylboronic catechol esters by
boron-transesterification with a substoichiometric amount of catechol
methyl borate (MeO–Bcat) telescoped onto a wide array of radical
chain processes. This simple one-pot, radical-chain, deboronative
protocol allows for the conversion of pinacol boronic esters into
iodides, bromides, chlorides, and thioethers. The process is also
suitable the formation of nitriles and allylated compounds via C–C
bond formation using sulfonyl radical traps. Finally, a particularly mild
protocol for the protodeboronation of pinacol boronic esters is given.
The power of combining radical and classical boron chemistry, is
illustrated with a highly modular 5-membered ring formation using a
combination of a three-component coupling reaction and a
protodeboronative cyclization