Activated Phenacenes from Phenylenes by Nickel-Catalyzed Alkyne Cycloadditions

被引：29

作者：

Gu, Zhenhua ^{[1
]}

Boursalian, Gregory B. ^{[1
]}

Gandon, Vincent ^{[2
]}

Padilla, Robin ^{[1
]}

Shen, Hao ^{[1
]}

Timofeeva, Tatiana V. ^{[3
]}

Tongwa, Paul ^{[3
]}

Vollhardt, K. Peter C. ^{[1
]}

Yakovenko, Andrey A. ^{[3
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

[2] Univ Paris 11, ICMMO, UMR CNRS 8182, F-91405 Orsay, France

[3] New Mexico Highlands Univ, Dept Nat Sci, Las Vegas, NM 87701 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 40期

基金：

美国国家科学基金会;

关键词：

aromatic compounds; cycloaddition; nickel; phenacenes; reaction mechanisms; POLYCYCLIC AROMATIC-COMPOUNDS; CARBON-CARBON BOND; GRAPHITE RIBBONS; BIPHENYLENE; COMPLEXES; CYCLOOCTATETRAENE; CLEAVAGE; BENZENE; PICENE; FAMILY;

D O I：

10.1002/anie.201103428

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Going zigzag, helical, or in-between: Angular phenylenes show a propensity for adding alkynes from the bay region in processes catalyzed by [Ni(cod)(PMe3)2] (see scheme). These transformations generate novel strain- and electronically activated phenacenes. Mechanistic studies in conjunction with DFT calculations (R=Ph) provide a plausible mechanistic picture. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：9413 / 9417

页数：5

共 40 条

[1]

[Anonymous], 2010, 826179 CCDC

[2] BIPHENYLENES .32. A NEW, GENERAL-SYNTHESIS OF MONO-BENZOBIPHENYLENE AND POLY-BENZOBIPHENYLENE FROM SUBSTITUTED BENZOCYCLOBUTENE-1,2-DIONES AND ORTHO-BIS(CYANOMETHYL)ARENES [J].

BUCKLAND, PR ;

HACKER, NP ;

MCOMIE, JFW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (07) :1443-1448

[3] Isolation of a Low-Coordinate Rhodium Phosphine Complex Formed by C-C Bond Activation of Biphenylene [J].

Chaplin, Adrian B. ;

Tonner, Ralf ;

Weller, Andrew S. .

ORGANOMETALLICS, 2010, 29 (12) :2710-2714

[4] Regiocontrolled Synthesis of Ethene-Bridged para-Phenylene Oligomers Based on PtII- and RuII-Catalyzed Aromatization [J].

Chen, Tse-An ;

Lee, Te-Ju ;

Lin, Ming-Yuan ;

Sohel, Shariar M. A. ;

Dian, Eric Wei-Guang ;

Lush, Shie-Fu ;

Liu, Rai-Shung .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (06) :1826-1833

[5] AROMATIC HYDROCARBONS .63. RESONANCE RESTRICTION AND THE ABSORPTION SPECTRA OF AROMATIC HYDROCARBONS [J].

CLAR, E ;

STEWART, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (24) :6235-6238

[6] BIPHENYLENES .33. SYNTHESIS OF BISBENZO[3,4]CYCLOBUTA[1,2-B, 1',2'-H] AND BISBENZO[3,4]CYCLOBUTA[1,2-C, 1',2'-G]-PHENANTHRENE, AND ATTEMPTS TO PREPARE PLANAR DERIVATIVES OF CYCLOOCTATETRAENE [J].

CRACKNELL, ME ;

KABLI, RA ;

MCOMIE, JFW ;

PERRY, DH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (01) :115-120

[7] Pyrolysis of a tubular aromatic compound [J].

Deichmann, M ;

Nather, C ;

Herges, R .

ORGANIC LETTERS, 2003, 5 (08) :1269-1271

[8] Large polycyclic aromatic hydrocarbons: Synthesis and discotic organization [J].

Feng, Xinliang ;

Pisula, Wojciech ;

Muellen, Klaus .

PURE AND APPLIED CHEMISTRY, 2009, 81 (12) :2203-2224

[9]

Gutman I, 2008, MATCH-COMMUN MATH CO, V60, P135

[10]

Haley M.M., 2006, CARBON RICH COMPOUND

← 1 2 3 4 →