Mild Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-23 DOI:10.1021/acs.orglett.5c0108810.1021/acs.orglett.5c01088

Austin J. Moser, Paige E. Sutter, Alex M. Chavez, Sebastian A. Cruz and Julian G. West*,

引用次数: 0

Abstract

Here we report the use of a tetrabutylammonium decatungstate (TBADT)/thiol photocatalytic system for selective addition of acetone and other simple ketone, nitrile, and chlorocarbon functionalities to terminal olefins. This system avoids the use of energetic reagents such as peroxides and proceeds under mild conditions using Earth-abundant element catalysts, providing a sustainable approach to C–C bond formation using activated olefins. Initial exploration reveals that hydroalkylation of unactivated olefins is also possible, though in lower efficiency, and preliminary mechanistic experiments are consistent with a radical mechanism.

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十钨酸盐/硫醇协同光催化催化末端烯烃轻度氢烷基化

在这里，我们报道了使用四丁基十钨酸铵(TBADT)/硫醇光催化体系选择性地将丙酮和其他简单酮、腈和氯碳官能团加成到末端烯烃上。该体系避免了使用过氧化物等高能试剂，在温和的条件下使用富含地球元素的催化剂，为使用活性烯烃形成C-C键提供了一种可持续的方法。初步的探索表明，非活化烯烃的氢烷基化也是可能的，尽管效率较低，初步的机理实验与自由基机理一致。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.