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Title: Nickel-catalyzed reductive coupling of unactivated alkyl bromides and aliphatic aldehydes
A mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides has been developed. The catalytic system features the use of a common Ni( ii ) precatalyst and a readily available bioxazoline ligand and affords silyl-protected secondary alcohols. The reaction is operationally simple, utilizing Mn as a stoichiometric reductant, and tolerates a wide range of functional groups. The use of 1,5-hexadiene as an additive is an important reaction parameter that provides significant benefits in yield optimizations. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species that undergoes formal oxidative addition to the alkyl bromide via a reductive cross-coupling pathway.  more » « less
Award ID(s):
1954939
NSF-PAR ID:
10323520
Author(s) / Creator(s):
;
Date Published:
Journal Name:
Chemical Science
Volume:
12
Issue:
36
ISSN:
2041-6520
Page Range / eLocation ID:
11995 to 12000
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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