香豆素的氧化剂控制区域选择性单官能化和双官能化反应。

Oxidant controlled regioselective mono- and di-functionalization reactions of coumarins.

作者信息

Banerjee Arghya, Santra Sourav Kumar, Khatun Nilufa, Ali Wajid, Patel Bhisma K

机构信息

Department of Chemistry, Indian Institute of Technology Guwahati, 781 039, Assam, India.

出版信息

Chem Commun (Camb). 2015 Oct 28;51(84):15422-5. doi: 10.1039/c5cc06200d.

DOI:10.1039/c5cc06200d

PMID:26343764

Abstract

C-3 alkylation of coumarins has been accomplished using cycloalkanes or alkylbenzenes in the presence of di-tert-butylperoxide (DTBP) and Fe(III) catalyst. Under metal free conditions and just by switching the oxidant from DTBP to TBHP, an exclusive C-4 cycloalkylation-C-3 peroxidation reaction takes place. During C-3 alkylation, the C-C bond formation occurs at the expense of an existing C-C bond, while the C-4 alkylation is associated with the formation of new C-C and C-O bonds.

摘要

在二叔丁基过氧化物（DTBP）和铁（III）催化剂存在的条件下，使用环烷烃或烷基苯已实现香豆素的C-3烷基化。在无金属条件下，只需将氧化剂从DTBP切换为叔丁基过氧化氢（TBHP），就会发生专一的C-4环烷基化-C-3过氧化反应。在C-3烷基化过程中，C-C键的形成是以牺牲现有的C-C键为代价的，而C-4烷基化则与新的C-C键和C-O键的形成有关。