Copper-Catalyzed Stereoselective Cyanation/Phosphorylation of Formamides with TMSCN and P(O)–H Bonds

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-12 DOI:10.1021/acs.orglett.5c01483

Weifeng Xu, Liyong Fan, Zikang Li, Longzhi Zhu, Min Liu, Biquan Xiong

引用次数: 0

Abstract

A novel copper-catalyzed approach for the stereoselective cyanation and phosphorylation of formamides has been developed. This protocol enables the direct conversion of a broad range of formamides and phosphorylation agents, including H-phosphonates, H-phosphinates, and H-phosphine oxides, into the target cyanation/phosphorylation products with good to excellent yields. Notably, when optically active H-phosphinates are employed, the transformation exhibits exceptional stereoselectivity. In combination with DFT calculation and systematic step-by-step control experiments, a possible reaction mechanism is proposed.

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铜催化具有TMSCN和P(O) -H键的甲酰胺的立体选择性氰化/磷酸化

提出了一种新的铜催化甲酰胺立体选择性氰化和磷酸化的方法。该方案能够将广泛的甲酰胺和磷酸化剂，包括h -膦酸盐，h -膦酸盐和h -膦氧化物，直接转化为具有良好至优异收率的目标氰化/磷酸化产物。值得注意的是，当采用光学活性h -膦酸盐时，转化表现出特殊的立体选择性。结合DFT计算和系统的分步控制实验，提出了一种可能的反应机理。

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.