Hyperconjugation-Driven Ester Migration Enabled Aerobic 1,3-Iodohydroxylation with Iodoform: A Triple Functionalization of Allyl Carboxylates

We report herein a visible-light-mediated aerobic 1,3-iodohydroxylation of allyl carboxylates using iodoform as an iodine source. This cascade reaction is initiated by the homolytic cleavage of the carbon-iodine bond in iodoform under visible light irradiation, generating an iodine radical, and triggers a cascade reaction of radical addition, ester migration, and hydroxylation. This practical trifunctionalization protocol features mild conditions and broad functional group tolerance.

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Publication Details

Journal
Organic Letters
Published
2026-04-15
DOI
https://doi.org/10.1021/acs.orglett.6c01136
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Hyperconjugation-Driven Ester Migration Enabled Aerobic 1,3-Iodohydroxylation with Iodoform: A Triple Functionalization of Allyl Carboxylates

Shaoqun Zhu, Linyang Jiang, Yun-Hee Han, Mengyan Gao et al.
Organic Letters
Radical Photochemical Reactions
article

Hyperconjugation-Driven Ester Migration Enabled Aerobic 1,3-Iodohydroxylation with Iodoform: A Triple Functionalization of Allyl Carboxylates

Shaoqun Zhu, Linyang Jiang, Yun-Hee Han, Mengyan Gao, Tao Lei, Pengpeng Zhu, Hong Hou
article en

Abstract

We report herein a visible-light-mediated aerobic 1,3-iodohydroxylation of allyl carboxylates using iodoform as an iodine source. This cascade reaction is initiated by the homolytic cleavage of the carbon-iodine bond in iodoform under visible light irradiation, generating an iodine radical, and triggers a cascade reaction of radical addition, ester migration, and hydroxylation. This practical trifunctionalization protocol features mild conditions and broad functional group tolerance.

Organic LettersVol. 28(16)
Yangzhou University (CN)
National Natural Science Foundation of China
Reduced inequalities
Openalex Percentile: Top 17%
Radical Photochemical Reactions
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