Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides

Aryl chlorides are more commercially available and lower cost compared with aryl bromides and iodides. However, the use of (hetero)aryl chlorides as aryl radical precursors for the di(hetero)arylation of alkenes remains an underdeveloped area. Furthermore, existing examples of theses reactions are predominantly confined to activated alkenes. In this study, we introduce a photoirradiation-promoted benzophenone-catalyzed 1,2-di(hetero)arylation process that is applicable to both activated and unactivated alkenes, utilizing (hetero)aryl chlorides and cyanoarenes as aryl sources. Importantly, this method allows for the simultaneous introduction of two heterocycles to alkenes with high regioselectivity.

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Publication Details

Journal
Organic Letters
Published
2025-05-01
DOI
https://doi.org/10.1021/acs.orglett.5c01269
Citations
4
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
3.74

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article

Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides

Bin Liu, Siqi Xie, Yingjun Lan
4 citations
Organic Letters
Catalytic C–H Functionalization Methods
3.74
article

Regioselective 1,2-Di(hetero)arylation of Activated and Unactivated Alkenes with (Hetero)aryl Chlorides

Bin Liu, Siqi Xie, Yingjun Lan
article en
4 citations

Abstract

Aryl chlorides are more commercially available and lower cost compared with aryl bromides and iodides. However, the use of (hetero)aryl chlorides as aryl radical precursors for the di(hetero)arylation of alkenes remains an underdeveloped area. Furthermore, existing examples of theses reactions are predominantly confined to activated alkenes. In this study, we introduce a photoirradiation-promoted benzophenone-catalyzed 1,2-di(hetero)arylation process that is applicable to both activated and unactivated alkenes, utilizing (hetero)aryl chlorides and cyanoarenes as aryl sources. Importantly, this method allows for the simultaneous introduction of two heterocycles to alkenes with high regioselectivity.

Organic LettersVol. 27(19)
Nanchang University (CN)
Natural Science Foundation of Jiangxi Province, Nanchang University
Openalex Percentile: Top 8%
Catalytic C–H Functionalization Methods
3.74
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