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Redox Chemistry of a Hydroxyphenyl‐Substituted Borane
Author(s) -
Feng PoYeng,
Liu YiHung,
Lin TienSung,
Peng ShieMing,
Chiu ChingWen
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201403247
Subject(s) - chemistry , borane , photochemistry , hydrogen atom abstraction , intramolecular force , redox , cobaltocene , hydrogen atom , hydride , benzoquinone , hydrogen , stereochemistry , organic chemistry , metallocene , catalysis , polymer , alkyl , polymerization
Chemical reduction of a hydroxyphenyl‐substituted borane triggers a sequential electron‐ and intramolecular hydrogen‐atom‐transfer process to afford a hydridoborate phenoxide dianion. On the other hand, hydrogen‐atom abstraction of the borane leads to the isolation of a neutral borylated phenoxyl radical, which can be transformed to the corresponding benzoquinone borataalkene derivative by reduction with cobaltocene.