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Highly Regioselective Nickel-Catalyzed Cross-Coupling of N-Tosylaziridines and Alkylzinc Reagents

Kim L. Jensen, Eric A. Standley and Timothy F. Jamison*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: tfjmit.edu

K. L. Jensen, E. A. Standley, T. F. Jamison, J. Am. Chem. Soc., 2014, 136, 11145-11152.

DOI: 10.1021/ja505823s (free Supporting Information)


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Abstract

A ligand-controlled, nickel-catalyzed cross-coupling of aliphatic N-tosylaziridines with aliphatic organozinc reagents offers complete regioselectivity for reaction at the less hindered C-N bond, and the products are furnished in very good yield for a broad selection of substrates. The air-stable nickel(II) chloride/ligand precatalyst can be handled and stored outside a glovebox.

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Key Words

amines


ID: J48-Y2014