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Cruz_04_03_21.pdf (889.28 kB)

Nickel-Catalyzed Reductive Coupling of Unactivated Alkyl Bromides and Aliphatic Aldehydes

preprint
submitted on 04.04.2021, 01:01 and posted on 05.04.2021, 14:17 by Cole Cruz, John Montgomery
We report the development of a mild, convenient coupling of aliphatic aldehydes and unactivated alkyl bromides. The catalytic system features the use of a common Ni(II) precatalyst and a readily available bisoxazoline 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. Initial mechanistic experiments support a mechanism featuring an alpha-silyloxy Ni species which undergoes formal oxidative addition of the alkyl bromide species via a reductive cross-coupling pathway.

Funding

National Science Foundation (CHE-1954939)

History

Email Address of Submitting Author

jmontg@umich.edu

Institution

University of Michigan

Country

United States

ORCID For Submitting Author

0000-0002-2229-0585

Declaration of Conflict of Interest

none

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