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Synthesis and Properties of 2,4,6‐Trimethylphenylborane (Mesitylborane), a Stable Alternative to Thexylborane
Author(s) -
Smith Keith,
Pelter Andrew,
Jin Zhao
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199408511
Subject(s) - regioselectivity , reagent , chemistry , stereochemistry , organic chemistry , catalysis
Four advantageous properties characterize mesitylborane MesBH 2 as a reagent: (1) It is readily accessible and quite stable. (2) It can be treated with two different 1‐alkenes in a stepwise fashion (→ MesBR 1 R 2 ). (3) The regioselectivity of each individual step is > 99%. (4) The products MesBR 1 R 2 can be readily transformed via MeOBR 1 R 2 or directly to BR 1 R 2 R 3 . MesBR 2 and BR 1 R 2 R 3 are important precursors for the synthesis of ketones R 1 R 2 CO and tertiary alcohols R 1 R 2 R 3 COH, respectively, by the cyanoborate process.