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Defluorinative Diborasodiation of Benzotrifluorides with Bis(pinacolato)Diboron and Sodium
Author(s) -
Ito Shiori,
Takahashi Fumiya,
Yorimitsu Hideki
Publication year - 2021
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202100206
Subject(s) - chemistry , halide , yield (engineering) , sodium , medicinal chemistry , organic chemistry , inorganic chemistry , metallurgy , materials science
Treatment of benzotrifluorides with sodium dispersion in the presence of bis(pinacolato)diboron results in diborative reduction to yield the corresponding diborylbenzylsodium species. The anionic species react not only with reactive organic halides but also with aromatic carbonyl compounds to yield the corresponding alkenylboron compounds via Peterson‐type olefination. The success of the generation of the diborylbenzylsodium species lies in immediate capture of initially formed unstable difluorobenzylsodium with co‐existing reduction‐resistant bis(pinacolato)diboron.