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Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

Niki R. Patel, Christopher B. Kelly, Matthieu Jouffroy and Gary A. Molander*

*Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

N. R. Patel, C. B. Kelly, M. Jouffroy, G. A. Molander, Org. Lett., 2016, 18, 764-767.

DOI: 10.1021/acs.orglett.6b00024 (free Supporting Information)


Abstract

Single-electron transmetalation via photoredox/nickel dual catalysis enables cross-coupling of primary and secondary (bis-catecholato)alkylsilicates with alkenyl halides via transfer of alkyl radicals under very mild reaction conditions. The method works with not only alkenyl bromides and iodides but also previously underexplored alkenyl chlorides.


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Thioetherification via Photoredox/Nickel Dual Catalysis

M. Jouffroy, C. B. Kelly, G. A. Molander, Org. Lett., 2016, 18, 876-879.


Key Words

Alkenes


ID: J54-Y2016