Hydroarylation of Alkynes Catalyzed by Nickel

被引：198

作者：

Nakao, Yoshiaki ^{[1
]}

机构：

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

来源：

CHEMICAL RECORD | 2011年 / 11卷 / 05期

关键词：

alkynes; C-H functionalization; hydroarylation; Lewis acids; nickel; C-H BONDS; PYRIDINE-N-OXIDES; DIRECT ARYLATION; SELECTIVE ALKENYLATION; INTRAMOLECULAR ARYLCYANATION; CIS-ADDITION; ATOM ECONOMY; ACTIVATION; ARYL; CARBOCYANATION;

D O I：

10.1002/tcr.201100023

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel catalysts derived from bis(1,5-cyclooctadiene) nickel [ Ni(cod)(2)] and trialkylphosphines effect hydroarylation of alkynes through functionalization of C-H bonds of arenes including benzo-fused five-membered heteroarenes, pyridine-N-oxides, pyridines, 2-pyridones, and perfluoroarenes. The reactions proceed with excellent stereo-and regioselectivity to give disubstituted arylethenes in good yields. Use of Lewis acid (LA) co-catalysts is crucial for success in reactions of imidazoles, pyridines, and 2-pyridones; it is possible that coordination of the LA to the nitrogen or oxygen functionalities of such substrates increases the reactivity of their C-H bonds towards nickel(0) species. DOI 10.1002/tcr.201100023

引用

页码：242 / 251

页数：10

共 99 条

[21] Pd-Catalyzed Oxidative Cross-Coupling of Perfluoroarenes with Aromatic Heterocycles [J].

He, Chun-Yang ;

Fan, Shilu ;

Zhang, Xingang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) :12850-12852

[22] Alkynylcyanation of alkynes and dienes catalyzed by nickel [J].

Hirata, Yasuhiro ;

Tanaka, Masaaki ;

Yada, Akira ;

Nakao, Yoshiaki ;

Hiyama, Tamejiro .

TETRAHEDRON, 2009, 65 (26) :5037-5050

[23] Nickel-Catalyzed Carbocyanation of Alkynes with Allyl Cyanides [J].

Hirata, Yasuhiro ;

Yukawa, Tomoya ;

Kashihara, Natsuko ;

Nakao, Yoshiaki ;

Hiyama, Tamejiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10964-10973

[24] REACTIONS OF BENZENES WITH ACETYLENES CATALYZED BY RHODIUM CARBONYL UNDER CARBON-MONOXIDE [J].

HONG, P ;

CHO, BR ;

YAMAZAKI, H .

CHEMISTRY LETTERS, 1979, (04) :339-342

[25] RHODIUM CARBONYL CLUSTER CATALYZED ADDITION OF ARENES TO DIPHENYLKETENE AND ARYL ISOCYANATES [J].

HONG, P ;

YAMAZAKI, H ;

SONOGASHIRA, K ;

HAGIHARA, N .

CHEMISTRY LETTERS, 1978, (05) :535-538

[26] CARBON HYDROGEN-BOND ACTIVATION BY A NICKEL-COMPLEX FOR THE CATALYTIC FORMATION OF DIENYNE SYSTEMS [J].

ISHIKAWA, M ;

OHSHITA, J ;

ITO, Y ;

MINATO, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (12) :804-805

[27] Efficient activation of aromatic C-H bonds for addition to C-C multiple bonds [J].

Jia, CG ;

Piao, DG ;

Oyamada, JZ ;

Lu, WJ ;

Kitamura, T ;

Fujiwara, Y .

SCIENCE, 2000, 287 (5460) :1992-1995

[28]

Joule J.A., 2000, Heterocyclic Chemistry, V4th, P63

[29] CATALYTIC ADDITION OF AROMATIC C-H BONDS TO ACETYLENES [J].

KAKIUCHI, F ;

YAMAMOTO, Y ;

CHATANI, N ;

MURAI, S .

CHEMISTRY LETTERS, 1995, (08) :681-682

[30] The ruthenium-catalyzed addition of β C-H bonds in aldehydes to olefins [J].

Kakiuchi, F ;

Sato, T ;

Igi, K ;

Chatani, N ;

Murai, S .

CHEMISTRY LETTERS, 2001, (05) :386-387

← 1 2 3 4 5 6 7 8 9 10 →