C-H arylation of triphenylene, naphthalene and related arenes using Pd/C

被引：87

作者：

Collins, Karl D. ^{[1
]}

Honeker, Roman ^{[1
]}

Vasquez-Cespedes, Suhelen ^{[1
]}

Tang, Dan-Tam D. ^{[1
]}

Glorius, Frank ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

CHEMICAL SCIENCE | 2015年 / 6卷 / 03期

关键词：

POLYCYCLIC AROMATIC-HYDROCARBONS; ONE-POT SYNTHESIS; CATALYZED AEROBIC DEHYDROGENATION; N BOND FORMATION; PALLADIUM CATALYSTS; HETEROGENEOUS CATALYSIS; CARBOXYLIC-ACIDS; ACTIVATION; FUNCTIONALIZATION; CARBON;

D O I：

10.1039/c4sc03051f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective arylation of a number of polyaromatic hydrocarbons (PAHs) with aryliodonium salts and Pd/C as the only reagent is reported. The first C-H functionalization of triphenylene is explored, and proceeds at the most sterically hindered position. This non-chelate assisted C-H functionalization extends the reactivity profile of Pd/C and provides controlled access to p-extended PAHs, an important aspect of work towards the preparation of nanographenes. Mechanistic studies suggest in situ formation of catalytically active insoluble nanoparticles, and that the reaction likely proceeds via a Pd(0)/Pd(II) type reaction manifold.

引用

页码：1816 / 1824

页数：9

共 123 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2] Palladium(0) nanoparticle-catalyzed sp2 C-H activation: a convenient route to alkyl-aryl ketones by direct acylation of aryl bromides and iodides with aldehydes [J].

Adak, Laksmikanta ;

Bhadra, Sukalyan ;

Ranu, Brindaban C. .

TETRAHEDRON LETTERS, 2010, 51 (29) :3811-3814

[3] Definitions of terms relating to the structure and processing of sols, gels, networks, and inorganic-organic hybrid materials (IUPAC Recommendations 2007) [J].

Aleman, J. ;

Chadwick, A. V. ;

He, J. ;

Hess, M. ;

Horie, K. ;

Jones, R. G. ;

Kratochvil, P. ;

Meisel, I. ;

Mita, I. ;

Moad, G. ;

Penczek, S. ;

Stepto, R. F. T. .

PURE AND APPLIED CHEMISTRY, 2007, 79 (10) :1801-1827

[4] Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis [J].

Allen, Anna E. ;

MacMillan, David W. C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4260-4263

[5] Honeycomb Carbon: A Review of Graphene [J].

Allen, Matthew J. ;

Tung, Vincent C. ;

Kaner, Richard B. .

CHEMICAL REVIEWS, 2010, 110 (01) :132-145

[6]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[7] Nanoparticles as recyclable catalysts: The frontier between homogeneous and heterogeneous catalysis [J].

Astruc, D ;

Lu, F ;

Aranzaes, JR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (48) :7852-7872

[8]

Augustine R.L., 1996, HETEROGENEOUS CATALY

[9] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[10] CONTROL OF ETA-2-ARENE COORDINATION AND C-H BOND ACTIVATION BY CYCLOPENTADIENYL COMPLEXES OF RHODIUM [J].

BELT, ST ;

DONG, LZ ;

DUCKETT, SB ;

JONES, WD ;

PARTRIDGE, MG ;

PERUTZ, RN .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (04) :266-269

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