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.

引用

页码：7742 / +

页数：3

共 38 条

[1] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[2] Synthesis of tricyclic quinolones and naphthyridones by intramolecular heck cyclization of functionalized electron-rich heterocycles
Beccalli, EM
Broggini, G
Martinelli, M
Paladino, G
Zoni, C
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (10) : 2091 - 2096
[3] A route to annulated indoles via a palladium-catalyzed tandem alkylation/direct arylation reaction
Bressy, C
Alberico, D
Lautens, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) : 13148 - 13149
[4] A solution to the 2-pyridyl organometallic cross-coupling problem:: Regioselective catalytic direct arylation of pyridine N-oxides
Campeau, LC
Rousseaux, S
Fagnou, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (51) : 18020 - 18021
[5] Chan KF, 2003, EUR J ORG CHEM, V2003, P82, DOI 10.1002/1099-0690(200301)2003:1<82::AID-EJOC82>3.0.CO
[6] 2-X
[7] Palladium-catalyzed arylation of electron-rich heterocycles with aryl chlorides
Chiong, Hendrich A.
Daugulis, Olafs
[J]. ORGANIC LETTERS, 2007, 9 (08) : 1449 - 1451
[8] Room temperature palladium-catalyzed 2-arylation of indoles
Deprez, NR
Kalyani, D
Krause, A
Sanford, MS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) : 4972 - 4973
[9] DESARBRE E, 1995, HETEROCYCLES, V41, P1987
[10] Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides
Dunetz, JR
Danheiser, RL
[J]. ORGANIC LETTERS, 2003, 5 (21) : 4011 - 4014

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