铁催化苯乙烯与脂肪醛和三甲基硅基叠氮化物通过脱羰烷基化-叠氮化级联反应进行自由基型双官能化反应。

Fe-Catalyzed radical-type difunctionalization of styrenes with aliphatic aldehydes and trimethylsilyl azide via a decarbonylative alkylation-azidation cascade.

作者信息

Li Wei-Yu, Wang Qi-Qiang, Yang Luo

机构信息

Key Laboratory for Environmentally Friendly Chemistry and Application of the Ministry of Education, Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan, 411105, PR China.

出版信息

Org Biomol Chem. 2017 Dec 6;15(47):9987-9991. doi: 10.1039/c7ob02598j.

DOI:10.1039/c7ob02598j

PMID:29170776

Abstract

A convenient Fe-catalyzed decarbonylative alkylation-azidation cascade reaction of styrene derivatives with aliphatic aldehydes and TMSN to provide aliphatic azides is developed. With DTBP as an oxidant and radical initiator, this reaction smoothly converts aliphatic aldehydes into 1°, 2° and 3° alkyl radicals and subsequently allows for the cascade construction of C(sp)-C(sp) and C(sp)-N bonds via radical insertion and nucleophilic azidation.

摘要

开发了一种方便的铁催化苯乙烯衍生物与脂肪醛和三甲基硅叠氮化物的脱羰烷基化-叠氮化串联反应，以提供脂肪族叠氮化物。以二叔丁基过氧化物（DTBP）作为氧化剂和自由基引发剂，该反应能顺利地将脂肪醛转化为伯、仲和叔烷基自由基，随后通过自由基插入和亲核叠氮化实现C(sp)-C(sp)和C(sp)-N键的串联构建。