Alkali-Metal-Catalyzed Deprotonative Addition of Toluenes with Styrenes.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-06 DOI:10.1021/acs.orglett.5c01842

Yuanyun Gu, Yufei Zhang, Yaqi Yuan, Yan-En Wang, Dan Xiong, Jianyou Mao

引用次数: 0

Abstract

A LiN(SiMe₃)₂/CsF-catalyzed benzylic C-H bond addition of toluene to styrene is reported, which enables the functionalization of weakly acidic C-H bonds (pK_a ≈ 43) with high efficiency and a broad substrate scope. This method overcomes the limitations of traditional strong base systems by utilizing a bimetallic catalyst that reversibly deprotonates benzylic positions, achieving yields of 62-89% across 34 examples. Key advantages include excellent functional group tolerance, scalability, and operational simplicity. Mechanistic studies, supported by kinetic isotope effects, confirm that benzylic deprotonation is the turnover-limiting step.

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碱金属催化甲苯与苯乙烯的脱质子加成反应。

本文报道了一种由LiN(SiMe3)2/ csf催化的苯类C-H键在苯乙烯上的加成反应，该反应使得弱酸性C-H键（pKa≈43）功能化效率高、底物范围广。该方法克服了传统强碱体系的局限性，利用双金属催化剂可逆地使苯基位置去质子化，34个样品的产率达到62-89%。主要优点包括出色的功能组容忍度、可伸缩性和操作简单性。动力学同位素效应支持的机理研究证实，苯基去质子化是限制周转的步骤。

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.