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Thioetherification via Photoredox/Nickel Dual Catalysis

Matthieu Jouffroy, Christopher B. Kelly 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

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

DOI: 10.1021/acs.orglett.6b00208 (free Supporting Information)



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Abstract

Alkyl radicals generated from hypervalent alkylsilicates serve as effective hydrogen atom abstractors from thiols, furnishing thiyl radicals. A subsequent nickel-mediated cross-coupling with aromatic bromides provides thioethers. This thioetherification of various aryl and heteroaryl bromides with a diverse array of thiols tolerates a wide range of functional groups due to the S-H selective H atom abstraction event.

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Engaging Alkenyl Halides with Alkylsilicates via Photoredox Dual Catalysis

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


Key Words

aryl sulfides


ID: J54-Y2016