Pursuing high efficiency in photocatalytic oxidative couplings of heteroarenes and aliphatic C-H bonds

被引：3

作者：

Zhang, Luoqiang ^{[1
,2
]}

Zhu, Dao-Yong ^{[2
]}

Hu, Jingyao ^{[1
]}

Feng, Minjun ^{[3
]}

Sum, Tze Chien ^{[3
]}

Sun, Haoran ^{[4
]}

Hirao, Hajime ^{[4
]}

Chi, Yonggui Robin ^{[2
]}

Zhou, Jianrong Steve ^{[1
]}

机构：

[1] Peking Univ, Sch Chem Biol & Biotechnol, State Key Lab Chem Oncogen, Guangdong Prov Key Lab Chem Genom,Shenzhen Grad Sc, 2199 Lishui Rd, Shenzhen 518055, Peoples R China

[2] Nanyang Technol Univ, Sch Chem Chem Engn & Biotechnol, Singapore 637371, Singapore

[3] Nanyang Technol Univ, Sch Phys & Math Sci, Div Phys & Appl Phys, 21 Nanyang Link, Singapore 637371, Singapore

[4] Chinese Univ Hong Kong, Warshel Inst Computat Biol, Sch Life & Hlth Sci, Sch Med, Shenzhen 518172, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 07期

基金：

中国国家自然科学基金; 新加坡国家研究基金会;

关键词：

LATE-STAGE FUNCTIONALIZATION; DIRECT ALPHA-ARYLATION; PYRIDINE N-OXIDES; DISSOCIATION ENERGIES; RADICAL ALKYLATION; MOLECULAR-OXYGEN; CROSS; METAL; ETHERS; C(SP(3))-H;

D O I：

10.1039/d2qo01558g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5- and 6-membered heteroarenes, both azoles and azines, were directly alkylated by alkanes, ethers and carbamates using t-butyl peroxybenzoate under LED irradiation. As a serendipitous finding, an organic photosensitizer, 9,10-dichloroanthracene, significantly increased overall efficiency of radical couplings via energy transfer of exciplexes and allowed many examples of oxidative couplings to proceed in good yields, even when 1.5 equivalents of alkanes were used.

引用

页码：1651 / 1659

页数：9

共 89 条

[1] Cross-dehydrogenative coupling of α-C(sp3)-H of ethers/alkanes with C(sp2)-H of heteroarenes under metal-free conditions [J].