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Direct Catalytic Desaturation of Lactams Enabled by Soft Enolization

Ming Chen and Guangbin Dong*

*Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States, Email: gbdonguchicago.edu

M. Chen. G. Dong, J. Am. Chem. Soc., 2017, 139, 7757-7760.

DOI: 10.1021/jacs.7b04722 (free Supporting Information)


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Abstract

A Pd-catalyzed α,β-desaturation of N-protected lactams provides conjugated unsaturated counterparts under mildly acidic conditions at room temperature. The reaction tolerates a wide range of functional groups and shows reactivity complementary to that of prior desaturation methods. Lactams with various ring sizes and substituents at different positions all reacted smoothly.

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Key Words

N-heterocycles, α,β-unsatured amides, 2,5-di-tert-butyl-1,4-benzoquinone, benzoquinone


ID: J48-Y2017