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

被引：11

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 50期

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

页码：18169 / 18178

页数：10

共 131 条

[11] Solvent-free aromatic C-H functionalisation/halogenation reactions [J].

Bedford, Robin B. ;

Engelhart, Jens U. ;

Haddow, Mairi F. ;

Mitchell, Charlotte J. ;

Webster, Ruth L. .

DALTON TRANSACTIONS, 2010, 39 (43) :10464-10472

[12] Copper(II) bromide: A simple and selective monobromination reagent for ElectronRich aromatic compounds [J].

Bhatt, Suchitra ;

Nayak, Sandip K. .

SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) :1381-1388

[13] Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides [J].

Blessley, George ;

Holden, Patrick ;

Walker, Matthew ;

Brown, John M. ;

Gouverneur, Veronique .

ORGANIC LETTERS, 2012, 14 (11) :2754-2757

[14] Evaluation of Industrially Applied Heat-Transfer Fluids as Liquid Organic Hydrogen Carrier Systems [J].

Brueckner, Nicole ;

Obesser, Katharina ;

Boesmann, Andreas ;

Teichmann, Daniel ;

Arlt, Wolfgang ;

Dungs, Jennifer ;

Wasserscheid, Peter .

CHEMSUSCHEM, 2014, 7 (01) :229-235

[15] Reversible Interconversion Between a Monomeric Iridium Hydroxo and a Dinuclear Iridium μ-Oxo Complex [J].

Burford, Richard J. ;

Piers, Warren E. ;

Ess, Daniel H. ;

Parvez, Masood .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (08) :3256-3263

[16] Simple palladium(II) precatalyst for Suzuki-Miyaura couplings: Efficient reactions of benzylic, aryl, heteroaryl, and vinyl coupling partners [J].

Burns, Michael J. ;

Fairlamb, Ian J. S. ;

Kapdi, Anant R. ;

Sehnal, Petr ;

Taylor, Richard J. K. .

ORGANIC LETTERS, 2007, 9 (26) :5397-5400

[17] ORGANOCOPPER INTERMIDIATES VIA DECARBOXYLATION OF CUPROUS CARBOXYLATES [J].

CAIRNCROSS, A ;

ROLAND, JR ;

HENDERSON, RM ;

SHEPPARD, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3187-+

[18] Site-selective Sp2 and benzylic Sp3 palladium-catalyzed direct arylation [J].

Campeau, Louis-Charles ;

Schipper, Derek J. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) :3266-+

[19] Palladium-Catalyzed Direct Arylation of C-H Bond To Construct Quaternary Carbon Centers: The Synthesis of Diarylfluorene [J].

Cao, Xiao ;

Yang, Weidong ;

Liu, Chao ;

Wei, Fuliang ;

Wu, Kun ;

Sun, Wei ;

Song, Juan ;

Xie, Linghai ;

Huang, Wei .

ORGANIC LETTERS, 2013, 15 (12) :3102-3105

[20] Gentisyl alcohol derivatives from the marine-derived fungus Penicillium terrestre [J].

Chen, Li ;

Fang, Yuchun ;

Zhu, Tianjiao ;

Gu, Qianqun ;

Zhu, Weiming .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (01) :66-70

← 1 2 3 4 5 6 7 8 9 10 →