Premium
Assessing the Brønsted Basicity of Diaminoboryl Anions: Reactivity toward Methylated Benzenes and Dihydrogen
Author(s) -
Dettenrieder Nicole,
Aramaki Yoshitaka,
Wolf Benjamin M.,
MaichleMössmer Cäcilia,
Zhao Xiaoxi,
Yamashita Makoto,
Nozaki Kyoko,
Anwander Reiner
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.201402175
Subject(s) - chemistry , deprotonation , toluene , medicinal chemistry , reactivity (psychology) , lithium (medication) , xylene , inorganic chemistry , nucleophilic substitution , ion , photochemistry , organic chemistry , medicine , alternative medicine , pathology , endocrinology
Treatment of toluene or p ‐xylene with diaminoboryllithium results in consecutive reactions, involving boryl‐anion‐mediated deprotonation at the benzylic position followed by nucleophilic substitution at the boron center, producing benzylborane species and LiH. Diaminoboryllithium also cleaves H 2 heterolytically affording diaminohydroborane and LiH, while the reaction of lithium diaminoboryl(bromo)cuprate with H 2 takes place accompanied by reduction of Cu I to give diaminohydroborane, LiH, and Cu 0 .