4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 49, Pages 16986-16989

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja5102695

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Funding

  1. NIHGMS [R01 GM103558-03]
  2. German Research Foundation (DFG)

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The photoredox-mediated coupling of benzylic ethers with Schiff bases has been accomplished. Direct benzylic CH activation by a combination of a thiol catalyst with an iridium photocatalyst and subsequent radicalradical coupling with secondary aldimines affords a variety of beta-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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