Rhodium(III)-Catalyzed Intermolecular Hydroarylation of Alkynes

被引：273

作者：

Schipper, Derek J. ^{[1
]}

Hutchinson, Marieke ^{[1
]}

Fagnou, Keith ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

C-H ACTIVATION; CATALYZED DIRECT ARYLATION; CARBON-HYDROGEN BONDS; INTERNAL ALKYNES; SIMPLE ARENES; FUNCTIONALIZATION; CLEAVAGE; MECHANISM; 2-PHENYLPYRIDINES; ALKENYLATION;

D O I：

10.1021/ja103080d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The rhodium(III)-catalyzed hydroarylation of internal alkynes is described. Good yields are obtained for a variety of alkynes, and excellent regioselectivity is observed for unsymmetrically substituted alkynes. The reaction also gives good yields for a range of arenes. Preliminary mechanistic investigations suggest that this reaction proceeds through arene metalation with the cationic rhodium catalyst, which enables challenging intermolecular reactivity.

引用

页码：6910 / +

页数：3

共 40 条

[1]

Ackermann L, 2007, TOP ORGANOMETAL CHEM, V24, P35, DOI 10.1007/3418_2007_062

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3] ALKYNE ACTIVATION BY ELECTROPHILIC [(ETA-C-5ME(5))RU(NO)(R)]+ (R=ME, PH, P-TOLYL) FRAGMENTS - BETA-MIGRATORY INSERTION, ISOMERIZATION, AND METALLACYCLE FORMATION [J].

BURNS, RM ;

HUBBARD, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) :9514-9520

[4] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[5]

Campeau LC, 2007, ALDRICHIM ACTA, V40, P35

[6] Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway [J].

Chernyak, Natalia ;

Gevorgyan, Vladimir .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (17) :5636-+

[7] Synthesis of Fluorenes via the Palladium-Catalyzed 5-exo-dig Annulation of o-Alkynylbiaryls [J].

Chernyak, Natalia ;

Gevorgyan, Vladimir .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (7-8) :1101-1114

[8] Regioselective functionalization of unreactive carbon-hydrogen bonds [J].

Daugulis, Olafs ;

Zaitsev, Vladimir G. ;

Shabashov, Dmitry ;

Pham, Quynh-Nhu ;

Lazareva, Anna .

SYNLETT, 2006, (20) :3382-3388

[9] Electrophilic C-H activation at {Cp*Ir}:: Ancillary-ligand control of the mechanism of C-H activation [J].

Davies, DL ;

Donald, SMA ;

Al-Duaij, O ;

Macgregor, SA ;

Pölleth, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) :4210-4211

[10] Computational study of the mechanism of cyclometalation by palladium acetate [J].

Davies, DL ;

Donald, SMA ;

Macgregor, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (40) :13754-13755

← 1 2 3 4 →