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Formation of Tertiary Amides and Dihydrogen by Dehydrogenative Coupling of Primary Alcohols with Secondary Amines Catalyzed by Ruthenium Bipyridine‐Based Pincer Complexes
Author(s) -
Srimani Dipankar,
Balaraman Ekambaram,
Hu Peng,
BenDavid Yehoshoa,
Milstein David
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300620
Subject(s) - chemistry , steric effects , ruthenium , pincer movement , primary (astronomy) , catalysis , acylation , organic chemistry , medicinal chemistry , combinatorial chemistry , physics , astronomy
Dehydrogenative coupling of primary alcohols with secondary amines to form tertiary amides and dihydrogen (H 2 ) is efficiently catalyzed by bipyridyl‐based ruthenium pincer complexes (0.2–1 mol%) under neutral conditions (in case of the dearomatized complexes), or with added catalytic amount of base. The reaction is sensitive to steric hindrance; in the case of amidation of bulky secondary amines a less sterically hindered complex is more efficient. Selective acylation of primary amines in the presence of secondary amines was also demonstrated.