Activation of C-H bonds via the merger of photoredox and organocatalysis: A coupling of benzylic ethers with schiff bases

Dominik Hager; David W.C. Macmillan

doi:10.1021/ja5102695

Activation of C-H bonds via the merger of photoredox and organocatalysis: A coupling of benzylic ethers with schiff bases

Dominik Hager, David W.C. Macmillan

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240 Scopus citations

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.

Original language	English (US)
Pages (from-to)	16986-16989
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	136
Issue number	49
DOIs	https://doi.org/10.1021/ja5102695
State	Published - Dec 10 2014

All Science Journal Classification (ASJC) codes

General Chemistry
Biochemistry
Catalysis
Colloid and Surface Chemistry

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10.1021/ja5102695

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title = "Activation of C-H bonds via the merger of photoredox and organocatalysis: A coupling of benzylic ethers with schiff bases",

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.",

author = "Dominik Hager and Macmillan, {David W.C.}",

note = "Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

year = "2014",

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Y1 - 2014/12/10

N2 - 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.

AB - 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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Activation of C-H bonds via the merger of photoredox and organocatalysis: A coupling of benzylic ethers with schiff bases

Abstract

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