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在碳酸二甲酯作为合适的替代溶剂中，铁催化α-重氮羰基化合物插入X-H键（X = Si、S、N和O）的反应。

Fe-catalysed insertion reaction of α-diazocarbonyls into X-H bonds (X = Si, S, N, and O) in dimethyl carbonate as a suitable solvent alternative.

作者信息

Tanbouza Nour, Keipour Hoda, Ollevier Thierry

机构信息

Département de Chimie, Université Laval 1045 Avenue de la Médecine Québec QC G1V 0A6 Canada.

出版信息

RSC Adv. 2019 Oct 2;9(54):31241-31246. doi: 10.1039/c9ra07203a. eCollection 2019 Oct 1.

DOI:10.1039/c9ra07203a
PMID:35527937
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9073380/
Abstract

The insertion reaction of a broad range of diazo compounds into Si-H bonds was found to be efficiently catalysed by Fe(OTf) in an emerging green solvent dimethyl carbonate (DMC). The α-silylated products were obtained in good to excellent yields (up to 95%). Kinetic studies showed that the extrusion of N to form an iron carbene intermediate is rate-limiting. The iron-catalysed insertion reaction of methyl α-phenyl-α-diazoacetate into polar X-H bonds (S-H, N-H, and O-H) was also established in DMC.

摘要

人们发现，在新兴的绿色溶剂碳酸二甲酯（DMC）中，多种重氮化合物插入Si-H键的反应能被Fe(OTf)有效催化。α-硅烷基化产物的产率良好至优异（高达95%）。动力学研究表明，氮的挤出以形成铁卡宾中间体是限速步骤。在DMC中也实现了铁催化的α-苯基-α-重氮乙酸甲酯插入极性X-H键（S-H、N-H和O-H）的反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/7446718a7399/c9ra07203a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/f8bb6acd307c/c9ra07203a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/f1593384e5f6/c9ra07203a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/7446718a7399/c9ra07203a-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/f8bb6acd307c/c9ra07203a-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/f1593384e5f6/c9ra07203a-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a7c1/9073380/7446718a7399/c9ra07203a-f3.jpg

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