Synthesis of 2,3-Disubstituted 1,4-Naphthoquinones via Metal-Free C(sp2)-H Functionalization Followed by Suzuki Cross-Coupling Reactions

被引：7
|
作者：
Borah, Ashwini [1 ,2 ]
Sharma, Abhilash [1 ,2 ]
Hazarika, Hemanta [1 ,2 ]
Gogoi, Pranjal [1 ,2 ]
机构：
[1] CSIR, North East Inst Sci & Technol, Appl Organ Chem Grp, Chem Sci & Technol Div, Jorhat 785006, Assam, India
[2] Acad Sci & Innovat Res AcSIR, CSIR NEIST Campus, Jorhat, Assam, India
来源：
CHEMISTRYSELECT | 2017年 / 2卷 / 31期
关键词：
Benzoylation; C(sp2)-H Functionalization; Metal-free; 1,4-Naphthoquinone; Suzuki-Cross Coupling; C-H FUNCTIONALIZATION; FRIEDEL-CRAFTS ACYLATION; DIRECT ARYLATION; ARYL; NAPHTHOQUINONES; DERIVATIVES; QUINONES; PHOTOCHEMISTRY; IDENTIFICATION; GENERATION;
D O I：
10.1002/slct.201702404
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A synthetic strategy has been developed for the synthesis of 2,3-disubstituted-1,4-naphthoquinones. This synthetic protocol consists of metal-free tert-Butyl hydroperoxide (TBHP)-mediated oxidative benzoylation followed by Pd-catalyzed Suzukicross coupling reactions. Benzaldehyde, benzylalcohol and toluene were efficiently used as benzoyl radical source for the benzoylation of 1,4-naphthoquinones. By this protocol, a wide range of 1,4-naphthoquinones with different substitution patterns were efficiently prepared in a sequential way with good to excellent yields.
引用
收藏
页码：9999 / 10003
页数：5
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