DPPF 催化的通过烯丙基自由基的原子转移自由基环化反应。

DPPF-Catalyzed Atom-Transfer Radical Cyclization via Allylic Radical.

机构信息

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.

School of Petrochemical Engineering, Changzhou University , 1 Gehu Road, Changzhou 213164, China.

出版信息

Org Lett. 2017 Dec 1;19(23):6328-6331. doi: 10.1021/acs.orglett.7b03135. Epub 2017 Nov 13.

DOI:10.1021/acs.orglett.7b03135

PMID:29130690

Abstract

A general iron-catalyzed strategy for the atom-transfer radical cyclization (ATRC) of allylic halide is reported. Critical to this strategy is the use of DPPF [1,1'-bis(diphenylphosphino)ferrocene] as catalyst, which allows for efficient generation of the allylic radical species via a single-electron transfer (SET) process. The feasibility of achieving ATRC reactions of propargyl chlorides is also demonstrated, which affords products with an exocyclic allene moiety.

摘要

本文报道了一种通用的铁催化的烯丙基卤化物原子转移自由基环化（ATRC）反应策略。该策略的关键是使用 DPPF [1,1'-双（二苯基膦基）二茂铁]作为催化剂，通过单电子转移（SET）过程有效地生成烯丙基自由基物种。还证明了炔丙基氯化物实现 ATRC 反应的可行性，该反应得到了具有环外丙二烯部分的产物。