Fasano, Valerio published the artcileDivergent, Stereospecific Mono- and Difluoromethylation of Boronic Esters, Computed Properties of 608534-44-7, the publication is Angewandte Chemie, International Edition (2020), 59(22), 8502-8506, database is CAplus and MEDLINE.
There is considerable interest in incorporating fluorine into agrochems. and pharmaceuticals to improve their biol. properties. While a number of methods have been reported for installing CH2F and CHF2 groups, they are mainly limited to radical reactions, which are invariably racemic. Herein, we report the divergent, stereospecific reaction of fluoroiodomethyllithium with boronic esters to give α-fluoro-boronic esters. These unique intermediates can be readily transformed into the corresponding mono- or difluoromethylated compounds through proto- or fluorodeboronation, resp. The use of the highly unstable fluoroiodomethyllithium was key to allowing rapid 1,2-migration over competing decomposition of the carbanion. DFT calculations informed and supported the exptl. findings. Thus, e.g., homologation of I with FCH2I/LDA → II (90%); protodeboronation using 4-tBu-catechol/TFA afforded III (90%).
Angewandte Chemie, International Edition published new progress about 608534-44-7. 608534-44-7 belongs to alcohols-buliding-blocks, auxiliary class Other Aromatic,Boronic acid and ester,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 2-(2,3-Dihydro-1H-inden-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, and the molecular formula is C15H21BO2, Computed Properties of 608534-44-7.
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