While suppressing the decomposition of trichloromethyl carbanions (generated from CHCl₃ using the LiOH base) to carbon monoxide and their participation in transmetallation and reductive elimination steps of cross-coupling’s catalytic cycle, a micelle-enabled catalytic carboxylation of (hetero)aryl halides is developed. The aqueous micelles play a crucial role in stabilizing both the highly reactive trichloromethyl carbanion and the single-metal atom catalyst to facilitate the desired reaction pathway efficiently. Comprehensive mechanistic analyses, including kinetic studies in the presence of trichloromethyl carbanion or carbon monoxide, H/D exchange via trichloromethyl anion, and mass spectrometric analysis of reaction intermediates, support a carbanion pathway. Simultaneously, the scope of this method was demonstrated over 40 substrates signifying broad functional and protecting group tolerance. This methodology was applied to the synthesis of isotopically enriched carboxylic acids using simple ¹⁸OH₂ and/or ¹³CHCl₃-labeled precursors.

中文翻译：

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水性胶束中的三氯甲基负碳离子：机理洞察和从（杂）芳基卤化物中获取羧酸

同时抑制三氯甲基负碳离子（由 CHCl _3生成使用 LiOH 碱）转化为一氧化碳并参与交叉偶联催化循环的金属转移和还原消除步骤，开发了（杂）芳基卤化物的胶束催化羧化。水性胶束在稳定高反应性三氯甲基负碳离子和单金属原子催化剂以有效促进所需反应途径方面起着至关重要的作用。综合机理分析，包括在三氯甲基负碳离子或一氧化碳存在下的动力学研究、通过三氯甲基阴离子进行的 H/D 交换以及反应中间体的质谱分析，支持负碳离子途径。同时，该方法的范围在 40 多种底物上得到了证明，这表明具有广泛的功能和保护基耐受性。¹⁸ OH ₂和/或¹³ CHCl ₃标记的前体。