Photocatalyst-free, visible-light-mediated C(sp3)-H arylation of amides via a solvent-caged EDA complex

Jaspreet Kaur; Ahmed Shahin; Joshua P. Barham

doi:10.1021/acs.orglett.1c00132

Photocatalyst-free, visible-light-mediated C(sp³)-H arylation of amides via a solvent-caged EDA complex

Jaspreet Kaur, Ahmed Shahin, Joshua P. Barham^*

^*Corresponding author for this work

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

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Abstract

A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.

Original language	English
Pages (from-to)	2002-2006
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	6
Early online date	17 Feb 2021
DOIs	https://doi.org/10.1021/acs.orglett.1c00132
Publication status	Published - 19 Mar 2021

Keywords

photocatalyst-free
visible light
C(sp3)-H arylation

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10.1021/acs.orglett.1c00132Licence: CC BY-NC-ND 4.0

Kaur-etal-OL-2021-Photocatalyst-free-visible-light-mediated-Csp3-H-arylation-of-amidesFinal published version, 1.64 MBLicence: CC BY-NC-ND 4.0

Cite this

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title = "Photocatalyst-free, visible-light-mediated C(sp3)-H arylation of amides via a solvent-caged EDA complex",

abstract = "A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.",

keywords = "photocatalyst-free, visible light, C(sp3)-H arylation",

author = "Jaspreet Kaur and Ahmed Shahin and Barham, \{Joshua P.\}",

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T1 - Photocatalyst-free, visible-light-mediated C(sp3)-H arylation of amides via a solvent-caged EDA complex

AU - Kaur, Jaspreet

AU - Shahin, Ahmed

AU - Barham, Joshua P.

PY - 2021/3/19

Y1 - 2021/3/19

N2 - A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.

AB - A photocatalyst-free and mild visible light photochemical procedure for C(sp3)-H arylation of amides is described. The reaction proceeds via an electron donor-acceptor (EDA) complex between an electron-rich arene substrate and electron-poor persulfate oxidant. C(sp3)-H arylation of the amide occurs selectively with the most electron-rich arene of the substrate. Mechanistic studies corroborate the reaction taking place in a solvent cage holding components in a close proximity.

KW - photocatalyst-free

KW - visible light

KW - C(sp3)-H arylation

U2 - 10.1021/acs.orglett.1c00132

DO - 10.1021/acs.orglett.1c00132

M3 - Article

C2 - 33596084

AN - SCOPUS:85101867525

SN - 1523-7060

VL - 23

SP - 2002

EP - 2006

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -