Premium
B(C 6 F 5 ) 3 ‐Catalyzed Transfer Hydrogenation of Imines and Related Heteroarenes Using Cyclohexa‐1,4‐dienes as a Dihydrogen Source
Author(s) -
Chatterjee Indranil,
Oestreich Martin
Publication year - 2015
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.201409246
Subject(s) - catalysis , transfer hydrogenation , transfer (computing) , chemistry , medicinal chemistry , organic chemistry , computer science , parallel computing , ruthenium
Abstract The strong boron Lewis acid tris(pentafluorophenyl)borane, B(C 6 F 5 ) 3 , is shown to abstract a hydride from suitably donor‐substituted cyclohexa‐1,4‐dienes, eventually releasing dihydrogen. This process is coupled with the FLP‐type (FLP=frustrated Lewis pair) hydrogenation of imines and nitrogen‐containing heteroarenes that are catalyzed by the same Lewis acid. The net reaction is a B(C 6 F 5 ) 3 ‐catalyzed, i.e., transition‐metal‐free, transfer hydrogenation using easy‐to‐access cyclohexa‐1,4‐dienes as reducing agents. Competing reaction pathways with or without the involvement of free dihydrogen are discussed.