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Switchable Cobalt-Catalyzed α-Olefination and α-Alkylation of Nitriles with Primary Alcohols

Keshav Paudel, Shi Xu and Keying Ding*

*Department of Chemistry, Middle Tennessee State University, Murfreesboro, Tennessee 37132, United States, Email: Keying.Dingmtsu.edu

K. Paudel, S. Xu, K. Ding, Org. Lett., 2021, 23, 5028-5032.

DOI: 10.1021/acs.orglett.1c01553 (free Supporting Information)



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Abstract

A well-defined base transition-metal Co complex catalyzes a switchable α-olefination and α-alkylation of nitriles with primary alcohols. A broad variety of nitriles and primary alcohols are selectively and efficiently converted to the corresponding vinyl nitriles. This environmentally benign and atom efficient transformation produces only H2 and H2O as byproducts.


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Proposed Mechanism (α-Olefination in Blue and α-Alkylation in Red)



α-Alkylation of Nitriles with Primary Alcohols by a Well-Defined Molecular Cobalt Catalyst

K. Paudell, S. Xu, K. Ding, J. Org. Chem., 2020, 85, 14980-14988.


Key Words

vinyl nitriles


ID: J54-Y2021