金(I)催化n -丙炔苯酰胺环化反应速率决定步骤的溶剂依赖性变化。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-07-28 DOI:10.1021/acs.joc.5c00787

Skylar G Norman,Lin Jiao,Jun Yi,Leo Liu,Wendu Ding,Amanda C Jones

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引用次数: 0

摘要

在过去的二十年里，n -丙炔苯酰胺与金催化剂的环化反应已经成为一种流行的基准反应。普遍的共识是，初始化是限速的。与[L1Au(NCCH3)]SbF6和L1AuOTs （L1 = t-Bu2（o-联苯）P，也称为约翰磷）在二氯甲烷和甲醇中的环化结合氘标记研究表明，在限速步骤中，溶剂依赖于π活化的转换。计算计算支持这种速率决定步骤的改变。

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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Solvent-Dependent Change in the Rate-Determining Step of Au(I)-Catalyzed N-Propargyl Benzamide Cyclization.

The cyclization of N-propargyl benzamide with gold catalysts has become a popular benchmark reaction over the past two decades. The prevailing consensus denotes protodeauration as rate-limiting. Cyclization with [L1Au(NCCH3)]SbF6 and L1AuOTs (L1 = t-Bu2(o-biphenyl)P, also known as Johnphos) in dichloromethane and methanol in conjunction with deuterium labeling studies reveals a solvent-dependent switch to π-activation for the rate-limiting step. Computational calculations support this change of the rate-determining step.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.