Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I(III)/S(VI) Ylides

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-01 DOI:10.1021/acs.orglett.5c00852

Shang-Shi Zhang, Jiaohang Wei, Qiong Hu, Zi-Feng Yang, Wen-Xuan Zou, Dan-Ting Shen, Mei-Zhu Bao, Xiang Liu

引用次数: 0

Abstract

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation of I^(III)/S^(VI) ylides with 1,3-dicarbonyls. By slight modification of the reaction conditions, controllable alkylation-hydroxylation and dialkylation of I^(III)/S^(VI) ylides were achieved. This strategy affords a diverse array of α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement in the [1,2]-sigmatropic rearrangement of sulfoxonium ylides and highlight the divergent reactivity of I^(III)/S^(VI) ylides.

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通过 I(III)/S(VI) Ylides 的 [1,2]-Sigmatropic Reearrangement/Akylation-Hydroxylation/Dialkylation 异构α,α-二官能化酮

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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.