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Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation

Shengzong Liang, Tatsuya Kumon, Ricardo A. Angnes, Melissa Sanchez, Bo Xu*, Gerald B. Hammond*

*Donghua University, Shanghai 201620, China; Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States, Email: bo.xudhu.edu.cn, gb.hammondLouisville.edu

S. Liang, T. Kumon, R. A. Angnes, M. Sanchez, B. Xu, G. B. Hammond, Org. Lett., 2019, 21, 3848-3854.

DOI: 10.1021/acs.orglett.9b01337 (free Supporting Information)


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Abstract

Under very mild oxidative conditions, 1,4-dihydropyridines (DHPs), derived from aldehydes, generate C(sp3)-radicals that couple with halogen radicals, which are generated from inexpensive halogen sources (NaBr, NaI, or HCl), to yield alkyl halides. The reaction tolerates a broad range of functional groups and achieves excellent site selectivity.

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Key Words

alkyl bromides, benzyl bromides, potassium peroxydisulfate, photochemistry


ID: J54-Y2019