Hydroheteroarylation of alkynes under mild nickel catalysis

被引：231

作者：

Nakao, Yoshiaki ^{[1
]}

Kanyiva, Kyalo Stephen ^{[1
]}

Oda, Shinichi ^{[1
]}

Hiyama, Tamejiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Kyoto 6158510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 25期

关键词：

D O I：

10.1021/ja0623459

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel complexes having a bulky tri(sec-alkyl)phosphine ligand catalyze hydroheteroarylation of alkynes at 35 °C. Selective activation of an Ar-H bond over an Ar-CN bond of N-protected 3-cyanoindoles is achieved by a proper choice of ligand and/or an N-protecting group. The catalysis is applicable to a diverse range of heteroarenes to afford cis-hydroheteroarylation products in highly chemo- and stereoselective manners. Excellent regioselectivity is observed with unsymmetrical alkynes to give the corresponding heteroaryl-substituted ethenes having a larger substituent trans to an aryl group. Copyright © 2006 American Chemical Society.

引用

页码：8146 / 8147

页数：2

共 53 条

[1] TRANSITION-METAL COMPLEXES OF DIAZENES .35. SYNTHESIS OF 1-(ARYLAMINO)INDOLES BY RODIUM-CATALYZED ADDITION OF ALKYNES TO 1,2-DIARYLDIAZENES [J].

AULWURM, UR ;

MELCHINGER, JU ;

KISCH, H .

ORGANOMETALLICS, 1995, 14 (07) :3385-3395

[2] Regioselective synthesis of 1,5-diaryl-1H-imidazoles by palladium-catalyzed direct arylation of 1-aryl-1H-imidazoles [J].

Bellina, F ;

Cauteruccio, S ;

Mannina, L ;

Rossi, R ;

Viel, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :3997-4005

[3] Kinetics, thermodynamics, and effect of BPh3 on competitive C-C and C-H bond activation reactions in the interconversion of allyl cyanide by [Ni(dippe)] [J].

Brunkan, NM ;

Brestensky, DM ;

Jones, WD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3627-3641

[4] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].

Campeau, LC ;

Parisien, M ;

Jean, A ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590

[5] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides [J].

Campeau, LC ;

Rousseaux, S ;

Fagnou, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) :18020-18021

[6] Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring [J].

Chatani, N ;

Fukuyama, T ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) :493-494

[7] Transition-metal-catalyzed reactions involving imidazolium salt/N-heterocyclic carbene couples as substrates [J].

Clement, ND ;

Cavell, KJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (29) :3845-3847

[8] Oxidative addition of imidazolium salts to Ni0 and Pd0:: Synthesis and structural characterization of unusually stable metal-hydride complexes [J].

Clement, ND ;

Cavell, KJ ;

Jones, C ;

Elsevier, CJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (10) :1277-1279

[9] Room temperature palladium-catalyzed 2-arylation of indoles [J].

Deprez, NR ;

Kalyani, D ;

Krause, A ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :4972-4973

[10] A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].

Dick, AR ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301

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