Highly Regioselective Syntheses of Substituted Triphenylenes from 1,2,4-Trisubstituted Arenes via a Co-Catalyzed Intermolecular Alkyne Cyclotrimerization

被引：35

作者：

Xu, Lingmin ^{[1
,2
]}

Yu, Ruocheng ^{[1
,2
]}

Wang, Yuefan ^{[1
,2
]}

Chen, Jiahua ^{[1
,2
]}

Yang, Zhen ^{[1
,2
,3
]}

机构：

[1] Peking Univ, Key Lab Bioorgan Chem & Mol Engn, Minist Educ, Beijing 100871, Peoples R China

[2] Peking Univ, BNLMS, Peking Tsinghua Ctr Life Sci, Coll Chem, Beijing 100871, Peoples R China

[3] Peking Univ, Shenzhen Grad Sch, Sch Chem Biol & Biotechnol, Lab Chem Genom, Shenzhen 518055, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 11期

基金：

美国国家科学基金会;

关键词：

TERMINAL ALKYNES; DIELS-ALDER; COBALT; CYCLOADDITION; CONSTRUCTION; MECHANISM; ENEDIYNES; RINGS;

D O I：

10.1021/jo400570b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report the development of a new method for the syntheses of substituted triphenylenes from the corresponding 1,2,4-trisubstituted arenes, which were themselves generated in a highly regioselective manner according to an intermolecular alkyne cyclotrimerization reaction that was catalyzed by a novel Co-TMTU complex. This highly regioselective reaction for the formation of 1,2,4-trisubstituted arenes will be a valuable addition to the plethora of tools already available to synthetic chemists and encourage further mechanistic studies of this important alkyne trimerization process.

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收藏

页码：5744 / 5750

页数：7

相关论文

共 44 条

[1] Cobalt-catalyzed cyclotrimerization of alkynes: The answer to the puzzle of parallel reaction pathways [J].

Agenet, Nicolas ;

Gandon, Vincent ;

Vollhardt, K. Peter C. ;

Malacria, Max ;

Aubert, Corinne .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (28) :8860-8871

[2] A NEW APPROACH TO THE CONSTRUCTION OF BIPHENYLENES BY THE COBALT-CATALYZED COCYCLIZATION OF ORTHO-DIETHYNYLBENZENES WITH ALKYNES - APPLICATION TO AN ITERATIVE APPROACH TO [3]PHENYLENE, THE 1ST MEMBER OF A NOVEL CLASS OF BENZOCYCLOBUTADIENOID HYDROCARBONS [J].

BERRIS, BC ;

HOVAKEEMIAN, GH ;

LAI, YH ;

MESTDAGH, H ;

VOLLHARDT, KPC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (20) :5670-5687

[3] Triphenylene-based discotic liquid crystals as self-assembled monolayers [J].

Boden, N ;

Bushby, RJ ;

Martin, PS ;

Evans, SD ;

Owens, RW ;

Smith, DA .

LANGMUIR, 1999, 15 (11) :3790-3797

[4] Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].

Boñaga, LVR ;

Zhang, HC ;

Moretto, AF ;

Ye, H ;

Gauthier, DA ;

Li, J ;

Leo, GC ;

Maryanoff, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485

[5]

BONNEMAN.H, 1974, SYNTHESIS-STUTTGART, P575

[6] Organometallic chemistry in supercritical water: metallorganic products of the CpCo-catalyzed cyclotrimerization of acetylenes [J].

Borwieck, H ;

Walter, O ;

Dinjus, E ;

Rebizant, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 570 (01) :121-127

[7] Efficient intermolecular [2+2+2] alkyne cyclotrimerization in aqueous medium using a ruthenium(IV) precatalyst [J].

Cadierno, Victorio ;

Garcia-Garrido, Sergio E. ;

Gimeno, Jose .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (47) :15094-15095

[8] Organoiridium compounds with bidentate phosphines as highly regioselective catalysts for alkynes cyclotrimerization [J].

Fabbian, M ;

Marsich, N ;

Farnetti, E .

INORGANICA CHIMICA ACTA, 2004, 357 (10) :2881-2888

[9] Air-Stable {(C5H5)Co} Catalysts for [2+2+2] Cycloadditions [J].

Geny, Anais ;

Agenet, Nicolas ;

Iannazzo, Laura ;

Malacria, Max ;

Aubert, Corinne ;

Gandon, Vincent .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (10) :1810-1813

[10] Can Electron-Rich π Systems Bind Anions? [J].

Geronimo, Inacrist ;

Singh, N. Jiten ;

Kim, Kwang S. .

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2011, 7 (04) :825-829

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