Photocatalytic Hydrodichloromethylation of Unactivated Alkenes with Chloroform

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-16 DOI:10.1021/acs.orglett.4c04367

Dawei Gong, Caiyu Gao, Yanlin Zhang, Fen Yao, Qixuan Li, Yufei Li, Lina Zhao, Degong Kong

引用次数: 0

Abstract

A visible-light-induced method for the hydrodichloromethylation of unactivated alkenes using chloroform (CHCl₃) was developed, employing pyridine·BH₃ as the halogen atom transfer (XAT) reagent. The strategy showed a broad functional group tolerance, and 29 examples of unactivated alkenes, including complex natural products or drug derivatives, have been established with good yields. Mechanistic studies indicated that CHCl₃ serves as both the source of a dichloromethyl radical and a hydrogen atom transfer (HAT) reagent, and the borane short-chain reaction process was involved in this system. This method represents a novel approach for hydrodichloromethylation of unactivated alkenes without using an additional HAT reagent.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.