Question

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Herein, we report on a detailed analysis of the traceless Staudinger ligation between a variety of phosphinothioesters (or phosphinoesters) and azides. Our analyses rely on isotopic labeling experiments and a continuous NMR-based assay for the reaction. These analyses reveal much new and useful information on the mechanism and kinetics of this versatile synthetic reaction.
Mechanism of the Staudinger Ligation. Our putative mechanism for the Staudinger ligation is shown in Scheme .The nitrogen atom of an iminophosphorane such as 1 has intrinsic nucleophilicity and can be acylated by a thioester (Scheme 1, path A). This acylation likely proceeds via
Scheme 1. Putative Mechanisms for the Staudinger Ligation Mediated by (Diphenylphosphino)methanethiol

Answer 1

在此，我们报告了各种phosphinothioesters（或phosphinoesters）和叠氮化物之间的无痕施陶丁格连接的详细分析。我们的分析依赖于同位素标记实验和连续的核磁共振测定该反应。这些分析揭示这种多功能合成反应的机理和动力学许多新的和有用的信息。
施陶丁格连接的机制。我们假定的机制施陶丁格连接方法示于方案。的膦亚胺的氮原子，例如1具有固有的亲核性，并且可以通过一个硫代酯（方案1中，路径A）酰化。这酰化可能通过进行
方案1。推定机制的施陶丁格连接介导的（二苯基膦）甲