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

页码：9999 / 10003

页数：5

共 50 条

[31] Metal-free oxidative tandem coupling of activated alkenes with carbonyl C(sp2)-H bonds and aryl C(sp2)-H bonds using TBHP
Zhou, Ming-Bo
Song, Ren-Jie
Ouyang, Xuan-Hui
Liu, Yu
Wei, Wen-Ting
Deng, Guo-Bo
Li, Jin-Heng
CHEMICAL SCIENCE, 2013, 4 (06) : 2690 - 2694
[32] Stereoselective C(sp2)-H Alkylation of Enamides with Unactivated Aliphatic Carboxylic Acids via Decarboxylative Cross-Coupling Reactions
Guo, Jing-Yu
Guan, Ting
Tao, Ji-Yu
Zhao, Kai
Loh, Teck-Peng
ORGANIC LETTERS, 2019, 21 (20) : 8395 - 8399
[33] Metal-Free C-2 Alkylation of N-Oxides with Ethers via Radical Cross-Coupling Reactions
Dong, Daoqing
Li, Guanghui
Chen, Demao
Sun, Yuanyuan
Han, Qingqing
Wang, Zuli
Xu, Xinming
Yu, Xianyong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1766 - 1771
[34] Transition-metal-free C(sp2)–C(sp3) cross-coupling of α-(pseudo)halo aliphatic ketones with boronic acids via a 1,4-metallate shift
Xue Li
Haohua Chen
Hao Wang
Qiaohui Zhang
Heyun Sheng
Yu Lan
Qiuling Song
Nature Synthesis, 2023, 2 : 1211 - 1221
[35] Transition-metal-free C(sp2)-C(sp3) cross-coupling of α-(pseudo)halo aliphatic ketones with boronic acids via a 1,4-metallate shift
Li, Xue
Chen, Haohua
Wang, Hao
Zhang, Qiaohui
Sheng, Heyun
Lan, Yu
Song, Qiuling
NATURE SYNTHESIS, 2023, 2 (12): : 1211 - 1221
[36] Transition-Metal-Free Oxidative Cross-Coupling of Methylhetarenes with Imidazoheterocycles towards Efficient C(sp2)-H Carbonylation
Sultana, Faria
Shaik, Siddiq Pasha
Alarifi, Abdullah
Srivastava, Ajay Kumar
Kamal, Ahmed
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (07) : 890 - 897
[37] Synthesis of 2-(2-Pyridyl)-2H-azirines via Metal-Free C-C Cross-Coupling of Bromoazirines with 2-Stannylpyridines
Agafonova, Anastasiya, V
Smetanin, Ilia A.
Rostovskii, Nikolai, V
Khlebnikov, Alexander F.
Novikov, Mikhail S.
ORGANIC LETTERS, 2021, 23 (20) : 8045 - 8049
[38] Metal-free photocatalyzed homo- and cross-dimerizations of α-hydroxyl ketones via dual C(sp3)-H functionalization: synthesis of 2,3-dihydroxyl-1,4-butanediones
Wang, Zhouying
Tang, Enrong
Zhou, Quanquan
Wan, Jie-Ping
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (04) : 1157 - 1162
[39] Novel and facile synthesis of 1-benzazepines via copper-catalyzed oxidative C(sp3)-H/C(sp2)-H cross-coupling
Wang, Rui
Jin, Ruo-Xing
Qin, Zi-Yang
Bian, Kang-Jie
Wang, Xi-Sheng
CHEMICAL COMMUNICATIONS, 2017, 53 (90) : 12229 - 12232
[40] C-H Functionalization of Imidazo[1,5-a]pyridines: A Metal-Free Approach for Methylene Insertion to Access C(sp2)-C(sp3)-H-C(sp2) Bond Formation
Mahajan, Shivangani
Sawant, Sanghapal D.
ACS OMEGA, 2024, 9 (50): : 49071 - 49080

← 1 2 3 4 5 →