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Direct Introduction of a Dimesitylboryl Group Using Base‐Mediated Substitution of Aryl Halides with Silyldimesitylborane
Author(s) -
Yamamoto Eiji,
Izumi Kiyotaka,
Shishido Ryosuke,
Seki Tomohiro,
Tokodai Noriaki,
Ito Hajime
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604021
Subject(s) - borylation , aryl , halide , chemistry , steric effects , biphenyl , borane , group (periodic table) , silylation , base (topology) , medicinal chemistry , organic chemistry , catalysis , mathematical analysis , mathematics , alkyl
The first dimesitylboryl substitution of aryl halides with a silylborane bearing a dimesitylboryl group in the presence of alkali‐metal alkoxides is described. The reactions of aryl bromides or iodides with Ph 2 MeSi−BMes 2 and Na(O t Bu) afforded the desired aryl dimesitylboranes in good to high yields and with high borylation/silylation ratios. Selective reaction of the sterically less‐hindered C−Br bond of dibromoarenes provided monoborylated products. This reaction was used to rapidly construct a D‐π‐A aryl dimesityl borane with a non‐symmetrical biphenyl spacer.