Minisci C–HAlkylation of Heterocycles withUnactivated Alkyl Iodides Enabled by Visible Light Photocatalysis

In this work, we developed a general catalytic strategy that allows Minisci C–H alkylation of a variety of heterocycles using unactivated alkyl halide as an alkyl radical source under visible light photocatalysis. Mild reaction conditions, employing 4CzIPN as an organophotocatalyst and aerial oxygen as a green terminal oxidant, a broad scope, good functional group tolerance, and late-stage C–H alkylation of bioactive and pharmaceutically relevant molecules are advantages of the protocol. Preliminary mechanistic studies indicate the involvement of the α-amino alkyl radical and the alkyl radical and further involvement of aerial oxygen under our reaction conditions.

Publication Details

Journal
Figshare
Published
2025-02-27
DOI
https://doi.org/10.1021/acs.joc.4c03151.s001
Primary Topic
Botany, Ecology, and Taxonomy Studies
Type
article
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article

Minisci C–HAlkylation of Heterocycles withUnactivated Alkyl Iodides Enabled by Visible Light Photocatalysis

Figshare
Botany, Ecology, and Taxonomy Studies
article

Minisci C–HAlkylation of Heterocycles withUnactivated Alkyl Iodides Enabled by Visible Light Photocatalysis

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Abstract

In this work, we developed a general catalytic strategy that allows Minisci C–H alkylation of a variety of heterocycles using unactivated alkyl halide as an alkyl radical source under visible light photocatalysis. Mild reaction conditions, employing 4CzIPN as an organophotocatalyst and aerial oxygen as a green terminal oxidant, a broad scope, good functional group tolerance, and late-stage C–H alkylation of bioactive and pharmaceutically relevant molecules are advantages of the protocol. Preliminary mechanistic studies indicate the involvement of the α-amino alkyl radical and the alkyl radical and further involvement of aerial oxygen under our reaction conditions.

Figshare
Openalex Percentile: Top 41%
Botany, Ecology, and Taxonomy Studies
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Minisci C–HAlkylation of Heterocycles withUnactivated Alkyl Iodides Enabled by Visible Light Photocatalysis · Figshare (2025) | TGRS Research Map | TGRS