Aerobic cross-dehydrogenative couplings of N-heteroarenes with toluene derivatives at room temperature

被引：29

作者：

Wang, Qiao-Lin ^{[1
]}

Huang, Huawen ^{[1
]}

Sun, Zhaozhao ^{[1
]}

Chen, Yufeng ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Key Lab Environmentally Friendly Chem & Applicat, Key Lab Green Organ Synth & Applicat Hunan Prov, Coll Chem,Minist Educ, Xiangtan 411105, Peoples R China

来源：

GREEN CHEMISTRY | 2021年 / 23卷 / 19期

基金：

中国国家自然科学基金;

关键词：

C-H BOND; REDUCTIVE MINISCI REACTION; BENZYLIC C(SP(3))-H BONDS; DIRECT ALPHA-ARYLATION; METAL-FREE; OXIDATIVE ACTIVATION; BENZYLATION; AMINATION; INDOLES; METHYLARENES;

D O I：

10.1039/d1gc02547c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A set of mild aerobic cross-dehydrogenative couplings of N-heteroarenes with the benzylic C(sp(3))-H bond has been achieved by using visible-light-induced photocatalysis. This approach was found to provide a sustainable alternative to Minisci benzylation reactions using readily accessible toluene derivatives as benzylating agents. The unique combination of photocatalysis, bromo radical mediation, and aerobic oxidation proved to be the key for the success of the transformation. Mechanistic studies revealed the feasibility of both oxidative and reductive quenching of the excited photocatalyst in the initial step.

引用

页码：7790 / 7795

页数：6

共 67 条

[1] Direct Selective Oxidative Cross-Coupling of Simple Alkanes with Heteroarenes
Antonchick, Andrey P.
Burgmann, Lars
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3267 - 3271
[2] Bond dissociation energies of organic molecules
Blanksby, SJ
Ellison, GB
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) : 255 - 263
[3] Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds
Borduas, Nadine
Powell, David A.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19) : 7822 - 7825
[4] Liquid-phase oxidation of alkylaromatics by a H-atom transfer mechanism with a new heterogeneous CoSBA-15 catalyst
Brutchey, RL
Drake, IJ
Bell, AT
Tilley, TD
[J]. CHEMICAL COMMUNICATIONS, 2005, (29) : 3736 - 3738
[5] Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles
Campos, Kevin R.
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1069 - 1084
[6] Picomole-Scale Real-Time Photoreaction Screening: Discovery of the Visible-Light-Promoted Dehydrogenation of Tetrahydroquinolines under Ambient Conditions
Chen, Suming
Wan, Qiongqiong
Badu-Tawiah, Abraham K.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (32) : 9345 - 9349
[7] Iron-Catalyzed Hetero-Cross-Dehydrogenative Coupling Reactions of Sulfoximines with Diarylmethanes: A New Route to N-Alkylated Sulfoximines
Cheng, Ying
Dong, Wanrong
Wang, Long
Parthasarathy, Kanniyappan
Bolm, Carsten
[J]. ORGANIC LETTERS, 2014, 16 (07) : 2000 - 2002
[8] Palladium-Catalyzed Minisci Reaction with Simple Alcohols
Correia, Camille A.
Yang, Luo
Li, Chao-Jun
[J]. ORGANIC LETTERS, 2011, 13 (17) : 4581 - 4583
[9] Copper-Catalyzed Cross-Dehydrogenative Coupling (CDC) of Alkynes and Benzylic C-H Bonds
Correia, Camille A.
Li, Chao-Jun
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (09) : 1446 - 1450
[10] Cross-dehydrogenative coupling of coumarins with Csp3-H bonds using an iron-organic framework as a productive heterogeneous catalyst
Doan, Son H.
Nguyen, Vu H. H.
Nguyen, Thuong H.
Pham, Phuc H.
Nguyen, Ngoc N.
Phan, Anh N. Q.
Tu, Thach N.
Phan, Nam T. S.
[J]. RSC ADVANCES, 2018, 8 (20): : 10736 - 10745

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