Copper-catalyzed aerobic oxidative amidation of terminal alkynes: Efficient synthesis of ynamides

被引：429

作者：

Hamada, Tetsuya ^{[1
]}

Ye, Xuan ^{[1
]}

Stahl, Shannon S. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 03期

关键词：

D O I：

10.1021/ja077406x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A copper-catalyzed method for the preparation of ynamides has been identified that proceeds via aerobic oxidative coupling of terminal alkynes with various nitrogen nucleophiles, including cyclic carbamates, amides and ureas, and N-alkyl-arylsulfonamides and indoles.

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页码：833 / +

页数：4

相关论文

共 56 条

[1] The copper-catalyzed N-arylation of indoles [J].

Antilla, JC ;

Klapars, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (39) :11684-11688

[2] 3-(4-IODOMETHYL-2-OXO-1-AZETIDINYL)PROPYNOIC ACID TERT-BUTYL ESTER - A NEW BETA-LACTAM DERIVATIVE, SYNTHESIS OF AN YNAMIDE BY REACTION OF 4-IODOMETHYLAZETIDIN-2-ONE WITH THE TERT-BUTYL ESTER OF PROPIOLIC ACID IN THE PRESENCE OF COPPER(I) [J].

BALSAMO, A ;

MACCHIA, B ;

MACCHIA, F ;

ROSSELLO, A ;

DOMIANO, P .

TETRAHEDRON LETTERS, 1985, 26 (34) :4141-4144

[3] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[4] Highly regio- and stereocontrolled synthesis of β-substituted α-tributylstannyl enamides [J].

Buissonneaud, D ;

Cintrat, JC .

TETRAHEDRON LETTERS, 2006, 47 (18) :3139-3143

[5] TERMINAL 1-HALO-1-ALKYNES AND 1-PSEUDOHALO-1-ALKYNES VIA BIS(TRIMETHYLSILYL)PEROXIDE (BTMSPO) PROMOTED UMPOLUNG TRANSFER OF HALIDES AND PSEUDOHALIDES [J].

CASARINI, A ;

DEMBECH, P ;

REGINATO, G ;

RICCI, A ;

SECONI, G .

TETRAHEDRON LETTERS, 1991, 32 (19) :2169-2170

[6] Practical synthesis of amides from in situ generated copper(I) acetylides and sulfonyl azides [J].

Cassidy, Michael P. ;

Raushel, Jessica ;

Fokin, Valery V. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (19) :3154-3157

[7] New N- and O-arylations with phenylboronic acids and cupric acetate [J].

Chan, DMT ;

Monaco, KL ;

Wang, RP ;

Winters, MP .

TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936

[8]

Chan DMT, 2005, BORONIC ACIDS: PREPARATION AND APPLICATIONS IN ORGANIC SYNTHESIS AND MEDICINE, P205, DOI 10.1002/3527606548.ch5

[9] Oxidative amide synthesis and N-terminal α-amino group ligation of peptides in aqueous medium [J].

Chan, Wing-Kei ;

Ho, Chi-Ming ;

Wong, Man-Kin ;

Che, Chi-Ming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) :14796-14797

[10] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

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