Photocatalyzed C(sp<sup>3</sup>)–N Bond Activation of Isonitriles for Mizoroki–Heck Cross-Coupling with Vinyl Arenes

We report a Mizoroki-Heck reaction enabled by the visible-light-induced Pd-catalyzed C-N bond cleavage of isonitriles. Through a one-carbon activation of amines, we eliminated the need for atom-inefficient activating groups, thereby allowing isonitriles to serve as alkyl radical precursors. The utility of this protocol was demonstrated with a variety of (hetero)aromatic-containing isonitriles and differentially substituted vinyl arenes. This transformation expands the range of cross-coupling reactions that amine precursors can undergo.

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Publication Details

Journal
Organic Letters
Published
2025-08-26
DOI
https://doi.org/10.1021/acs.orglett.5c02954
Citations
3
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

Photocatalyzed C(sp3)–N Bond Activation of Isonitriles for Mizoroki–Heck Cross-Coupling with Vinyl Arenes

Alexander W. Schuppe, Seunho Jung, Andrew Wood, N. Mizuno
3 citations
Organic Letters
Catalytic Cross-Coupling Reactions
2.81
article

Photocatalyzed C(sp3)–N Bond Activation of Isonitriles for Mizoroki–Heck Cross-Coupling with Vinyl Arenes

Alexander W. Schuppe, Seunho Jung, Andrew Wood, N. Mizuno
article en
3 citations

Abstract

We report a Mizoroki-Heck reaction enabled by the visible-light-induced Pd-catalyzed C-N bond cleavage of isonitriles. Through a one-carbon activation of amines, we eliminated the need for atom-inefficient activating groups, thereby allowing isonitriles to serve as alkyl radical precursors. The utility of this protocol was demonstrated with a variety of (hetero)aromatic-containing isonitriles and differentially substituted vinyl arenes. This transformation expands the range of cross-coupling reactions that amine precursors can undergo.

Organic LettersVol. 27(35)
Vanderbilt University (US)
Vanderbilt University, Chiba University, National Institute of General Medical Sciences
Openalex Percentile: Top 9%
Catalytic Cross-Coupling Reactions
2.81
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