Copper-catalyzed redox neutral ketoalkylation of Csp2-H bonds via C-C bond cleavage

被引：11

作者：

Chen, He

Guo, Li-Na

Sun, Qing-Xin

Chen, Lei

Tao, Jing-Qi

Gao, Pin ^{[1
]}

机构：

[1] Xi An Jiao Tong Univ, Xian Key Lab Sustainable Energy Mat Chem, Sch Chem, Dept Chem, Xian 710049, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 20期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

HETEROAROMATIC N-OXIDES; CYCLOALKYLSILYL PEROXIDES; H FUNCTIONALIZATION; ALKYLATION; INHIBITORS; QUINOXALIN-2(1H)-ONES; DERIVATIVES; CYCLIZATION; QUINONES; RADICALS;

D O I：

10.1039/d1qo00882j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient copper-catalyzed ketoalkylation of Csp(2)-H bonds with cycloalkyl silyl peroxides under mild and redox neutral conditions is presented. Relying on the C-C bond cleavage, a series of distal ketoalkyl moieties were successfully incorporated into the specific position of quinoxalin-2(1H)-ones, heteroaromatic N-oxides and quinones with moderate to good yields.

引用

页码：5866 / 5871

页数：6

共 50 条

[1] Copper-Catalyzed Methyl Esterification Reactions via C-C Bond Cleavage
Zhu, Yan
Yan, Hong
Lu, Linhua
Liu, Defu
Ron, Guangwei
Mao, Jincheng
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9898 - 9905
[2] Iron catalyzed ketoalkylation and ketoalkylation/etherification of styrenes initiated by selective C-C bond cleavage
Suo, Meng-Ting
Yang, Shuo
Yang, Jun-Cheng
Liu, Ze-Yu
Zhang, Jun-Jie
Guo, Li-Na
ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) : 2414 - 2418
[3] Copper-catalyzed borylation of cycloalkylsilyl peroxides via radical C-C bond cleavage
Yang, Jun-Cheng
Chen, Lei
Yang, Fan
Li, Pengfei
Guo, Li-Na
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (15): : 2792 - 2795
[4] Copper-catalyzed oxidative amidation of α,β-unsaturated ketones via selective C-H or C-C bond cleavage
Pouambeka, Tony Wheellyam
Zhang, Ge
Zheng, Guang-Fan
Xu, Guo-Xing
Zhang, Qian
Xiong, Tao
Zhang, Qian
ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1420 - 1424
[5] Copper-Catalyzed N-Benzoylation of Amines via Aerobic C-C Bond Cleavage
Fan, Wenyou
Yang, Youqing
Lei, Jianhua
Jiang, Qijian
Zhou, Wang
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (17): : 8782 - 8789
[6] Copper-catalyzed silylations of C-C π-bonds
Harruff, Stephan
Mikesell, Brandon
Van Hoveln, Ryan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
[7] Copper-catalyzed aerobic radical C-C bond cleavage of N-H ketimines
Tnay, Ya Lin
Ang, Gim Yean
Chiba, Shunsuke
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1933 - 1943
[8] Efficient synthetic route to bisaryl ketones via copper-catalyzed C-C triple bonds cleavage
Li, Xiangguang
Huang, Wenzhong
Liang, Deqiang
Yuan, Lin
Ma, Yinhai
Gu, Lijun
TETRAHEDRON, 2015, 71 (07) : 1045 - 1049
[9] Copper-Catalyzed Intramolecular C-C Bond Cleavage To Construct 2-Substituted Quinazolinones
Hu, Ben-Quan
Wang, Li-Xia
Yang, Luo
Xiang, Jun-Feng
Tang, Ya-Lin
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (20) : 4504 - 4509
[10] Copper-Catalyzed Aza-Benzyl Transfer Michael Addition via C-C Bond Cleavage
Xiong, Si-Qi
Hong, Chuan-Ming
Li, Qing-Hua
Liu, Tang -Lin
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (06): : 3523 - 3531

← 1 2 3 4 5 →