Organic Chemistry Portal

Abstracts

Search:

Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates

Matthieu Jouffroy, David N. Primer and Gary A. Molander*

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

M. Jouffroy, D. N. Primer, G. A. Molander, J. Am. Chem. Soc., 2016, 138, 475-478.

DOI: 10.1021/jacs.5b10963 (free Supporting Information)


Abstract

Hypercoordinate silicates represent an improved class of radical precursors for single-electron transmetalation because of their low oxidation potentials and the innocuous byproducts generated upon oxidation. The cross-coupling of secondary and primary ammonium alkylsilicates with (hetero)aryl bromides works in good to excellent yields.


see article for more examples



Key Words

alkylation


ID: J48-Y2016