Activation of C-H Bonds Via the Merger of Photoredox and Organocatalysis: a Coupling of Benzylic Ethers with Schiff Bases

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2014 Dec 3

PMID 25457231

Citations 46

Authors

Dominik Hager

David W C MacMillan

Affiliations

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Abstract

The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic C-H activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radical-radical coupling with secondary aldimines affords a variety of β-amino ether products in good to excellent yields. Mechanistic studies suggest that a reductive quenching pathway of the photocatalyst is operable.

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