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Tris(2,4,6‐trifluorophenyl)borane: An Efficient Hydroboration Catalyst
Author(s) -
Lawson James R.,
Wilkins Lewis C.,
Melen Rebecca L.
Publication year - 2017
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.201703109
Subject(s) - pinacol , hydroboration , borane , chemistry , catalysis , organic chemistry , boranes , reagent , tris , amine gas treating , quinoxaline , diborane , combinatorial chemistry , boron , biochemistry
The metal‐free catalyst tris (2,4,6‐trifluorophenyl)borane has demonstrated its extensive applications in the 1,2‐hydroboration of numerous unsaturated reagents, namely alkynes, aldehydes and imines, consisting of a wide array of electron‐withdrawing and donating functionalities. A range of over 50 borylated products are reported, with many reactions proceeding with low catalyst loading under ambient conditions. These pinacol boronate esters, in the case of aldehydes and imines, can be readily hydrolyzed to leave the respective alcohol and amine, whereas alkynyl substrates result in vinyl boranes. This is of great synthetic use to the organic chemist.