Cross-Dehydrogenative-Coupling of Alkoxybenzenes with Toluenes: Copper(II) Halide Mediated Tandem Halo/Benzylation of Arenes

被引:12
作者
Storr, Thomas E. [1 ]
Teskey, Christopher J. [1 ]
Greaney, Michael F. [1 ]
机构
[1] Univ Manchester, Sch Chem, Oxford Rd, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
C-H activation; cross-dehydrogenative-coupling; diarylmethane; homogeneous catalysis; tandem reactions; C-H BOND; CATALYZED DIRECT ARYLATION; SITE-SELECTIVE SP(2); ANTIMICROBIAL ACTIVITIES; METAL-FREE; PALLADIUM; ARYL; FUNCTIONALIZATION; DIARYLMETHANES; BROMOPHENOLS;
D O I
10.1002/chem.201603783
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A cross-dehydrogenative-coupling of alkoxybenzenes and toluenes with concomitant halogenation is reported. Conditions employed were the use of stoichiometric copper halide salts and dialkylperoxides to afford a range of bromoalkoxydi- and triarylmethanes. Preliminary mechanistic studies suggest that the in situ production of haloarenes (or dihaloarenes) followed by a copper-mediated coupling of a benzylic radical is operational.
引用
收藏
页码:18169 / 18178
页数:10
相关论文
共 131 条
[51]   A simple preparation of diarylmethanes by oxidative friedel-crafts reaction of methyl-substituted benzenes with o-chloranil [J].
Kobayashi, T ;
Rahman, SM .
SYNTHETIC COMMUNICATIONS, 2003, 33 (22) :3997-4003
[52]   SELECTIVE NUCLEAR HALOGENATION OF POLYMETHYLBENZENES WITH ALUMINA-SUPPORTED COPPER(II) HALIDES [J].
KODOMARI, M ;
SATOH, H ;
YOSHITOMI, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (11) :4149-4150
[53]   Pd(II)-catalyzed Chelation-assisted Cross Dehydrogenative Coupling between Unactivated C(sp3)-H Bonds in Aliphatic Amides and Benzylic C-H Bonds in Toluene Derivatives [J].
Kubo, Teruhiko ;
Aihara, Yoshinori ;
Chatani, Naoto .
CHEMISTRY LETTERS, 2015, 44 (10) :1365-1367
[54]   C(sp3)-H Bond Arylations Catalyzed by Well-Defined [Ru(O2CMes)2(p-cymene)] [J].
Kumar, N. Y. Phani ;
Jeyachandran, Rajkumar ;
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) :4145-4152
[55]   Palladium-Catalyzed Synthesis of Heterocycle-Containing Diarylmethanes through Suzuki-Miyaura Cross-Coupling [J].
Kuriyama, Masami ;
Shinozawa, Mina ;
Hamaguchi, Norihisa ;
Matsuo, Seira ;
Onomura, Osamu .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12) :5921-5928
[56]   Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations [J].
Li, Chao-Jun .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (02) :335-344
[57]   Cross-Coupling of Grignard Reagents with Sulfonyl-Activated sp3 Carbon-Nitrogen Bonds [J].
Li, Man-Bo ;
Tang, Xiang-Ling ;
Tian, Shi-Kai .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (11-12) :1980-1984
[58]   A facile, regioselective and controllable bromination of aromatic amines using a CuBr2/Oxone® system [J].
Li, Xin-Le ;
Wu, Wei ;
Fan, Xin-Heng ;
Yang, Lian-Ming .
RSC ADVANCES, 2013, 3 (30) :12091-12095
[59]   Nickel-Catalyzed Reductive Cross-Coupling of (Hetero)Aryl Iodides with Fluorinated Secondary Alkyl Bromides [J].
Li, Xuefei ;
Feng, Zhang ;
Jiang, Zhong-Xing ;
Zhang, Xingang .
ORGANIC LETTERS, 2015, 17 (22) :5570-5573
[60]   Cross Dehydrogenative Arylation (CDA) of a Benzylic C-H Bond with Arenes by Iron Catalysis [J].
Li, Yi-Zhou ;
Li, Bi-Jie ;
Lu, Xing-Yu ;
Lin, Song ;
Shi, Zhang-Jie .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (21) :3817-3820