Direct palladium-catalyzed alkynylation of N-fused heterocycles

被引：253

作者：

Seregin, Ilya V. ^{[1
]}

Ryabova, Victoria ^{[1
]}

Gevorgyan, Vladimir ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 25期

关键词：

D O I：

10.1021/ja072718l

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of direct C-H alkynylation of electron-rich heteroaromatics has been demonstrated. This mild, simple, and general method allows for the efficient synthesis of diverse alkynyl heterocycles. Kinetic isotope effect studies support an electrophilic substitution pathway for this transformation.

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页码：7742 / +

页数：3

相关论文

共 38 条

[11] A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].

Frederick, MO ;

Mulder, JA ;

Tracey, MR ;

Hsung, RP ;

Huang, J ;

Kurtz, KCM ;

Shen, LC ;

Douglas, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369

[12] INDIUM-CATALYZED CYCLOISOMERIZATION: PREPARATION OF 4-METHYLPYRROLO[1,2-a] QUINOLINE [J].

Fuerstner, Alois ;

Mamane, Victor ;

Seidel, Guenter ;

Laurich, Daniel .

ORGANIC SYNTHESES, 2006, 83 :103-+

[13] Proton abstraction mechanism for the palladium-catalyzed intramolecular arylation [J].

García-Cuadrado, D ;

Braga, AAC ;

Maseras, F ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1066-1067

[14] Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions [J].

Giri, R ;

Chen, X ;

Yu, JQ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (14) :2112-2115

[15] Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene [J].

Glover, B ;

Harvey, KA ;

Liu, B ;

Sharp, MJ ;

Tymoschenko, MF .

ORGANIC LETTERS, 2003, 5 (03) :301-304

[16]

Hashmi ASK, 2000, ANGEW CHEM INT EDIT, V39, P2285, DOI 10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO

[17]

2-F

[18]

HOLLINGWORTH GJ, 1993, SYNLETT, P463

[19] Isotope effects in C-H bond activation reactions by transition metals [J].

Jones, WD .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (02) :140-146

[20] Polymer support assisted selective functionalization of azoles using a palladium-catalyzed coupling reaction [J].

Kondo, Y ;

Komine, T ;

Sakamoto, T .

ORGANIC LETTERS, 2000, 2 (20) :3111-3113

← 1 2 3 4 →