Bismuth-catalyzed methylation and alkylation of quinone derivatives with tert-butyl peroxybenzoate as an oxidant

被引：12

作者：

Yang, Jian ^{[1
,2
]}

Dong, Yu ^{[1
,2
]}

He, Shuai ^{[3
]}

Shi, Zhi-Chuan ^{[3
]}

Wang, Yu ^{[4
]}

Wang, Ji-Yu ^{[1
]}

机构：

[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610041, Sichuan, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Southwest Minzu Univ, Chengdu 610041, Sichuan, Peoples R China

[4] Guizhou Educ Univ, Guiyang 550018, Guizhou, Peoples R China

来源：

TETRAHEDRON | 2019年 / 75卷 / 50期

关键词：

Quinone derivatives; Methylation; Alkylation; Bismuth (III) trifluoromethanesulfonate ten-Butyl peroxybenzoate; C(SP(3))-H BOND FUNCTIONALIZATION; METAL-FREE; OXIDATIVE CYCLIZATION; ARYLATION; ACCESS; ALLYLATION; THYMOQUINONE; CINNAMAMIDES; AMINATION; SULFONES;

D O I：

10.1016/j.tet.2019.130729

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A bismuth-catalyzed methylation of quinones in the presence of tert-butyl peroxybenzoate (TBPB) was developed via a radical reaction mechanism. Particularly, TBPB was used not only as an efficient oxidant, but also as a green methyl source in such transformation. Moreover, this method could also be efficiently extended to the alkylation of quinones. This reaction tolerated a series of functional groups and prepared a series of derivatives of vitamin K-3 and benzoquinone. Notably, antimalarial parvaquone was synthesized by the reaction. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页数：7

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