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通过 Fe 催化的α-重氮羰基化合物插入 S-H 键合成α-硫代羰基化合物。

α-Thiocarbonyl synthesis via the Fe-catalyzed insertion reaction of α-diazocarbonyls into S-H bonds.

机构信息

Département de chimie, Université Laval, 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada.

出版信息

Org Biomol Chem. 2019 Mar 20;17(12):3098-3102. doi: 10.1039/c9ob00261h.

DOI:10.1039/c9ob00261h
PMID:30834409
Abstract

Fe(OTf)2 was used to catalyze the insertion reaction of α-diazocarbonyls into S-H bonds at 40 °C. A wide range of α-thioesters were obtained in yields up to 96% within 24-48 h from their corresponding α-diazoesters. A variety of thiols were used for the unprecedented insertion reaction with an α-diazoketone, leading to yields up to 85% of α-thioketones.

摘要

Fe(OTf)2 用于催化 α-二羰基化合物在 40°C 下插入 S-H 键。在 24-48 小时内,从相应的 α-重氮酯可得到产率高达 96%的α-硫代酯。各种硫醇用于前所未有的α-二氮酮的插入反应,得到产率高达 85%的α-硫代酮。

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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。
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