Understanding Catalytic Enantioselective C–H Bond Oxidation at Nonactivated Methylenes Through Predictive Statistical Modeling Analysis

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-01-22 DOI:10.1021/acscatal.4c05659

Arnau Call, Andrea Palone, Jordan P. Liles, Natalie P. Romer, Jacquelyne A. Read, Josep M. Luis, Matthew S. Sigman, Massimo Bietti, Miquel Costas

引用次数: 0

Abstract

Enantioselective C(sp³)–H bond oxidation is a powerful strategy for installing functionality in C(sp³)–H rich molecules. Site- and enantioselective oxidation of strong C–H bonds in monosubstituted cyclohexanes with hydrogen peroxide catalyzed by aminopyridine manganese catalysts in combination with alkanoic acids has been recently described. Mechanistic uncertainties and nonobvious enantioselectivity trends challenge development of the full potential of this reaction as a powerful synthetic tool. Herein, we apply predictive statistical analysis to identify mechanistically informative correlations that provide valuable reaction understanding and will guide the future development and optimization of enantioselective C–H oxidation reactions.

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通过预测统计模型分析了解非活化亚甲基的催化对映选择性C-H键氧化

对映选择性C(sp3) -H键氧化是在富C(sp3) -H分子中安装功能的一种有效策略。氨基吡啶锰催化剂与烷烃酸结合催化过氧化氢对单取代环己烷中强碳氢键进行了位点选择性和对映选择性氧化。机制的不确定性和不明显的对映体选择性趋势挑战了该反应作为强大合成工具的全部潜力的发展。在此，我们应用预测统计分析来确定机制信息相关性，提供有价值的反应理解，并将指导未来对映选择性C-H氧化反应的开发和优化。

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

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.