Direct Alkynylation of Indole and Pyrrole Heterocycles

被引：359

作者：

Brand, Jonathan P. ^{[1
]}

Charpentier, Julie ^{[1
]}

Waser, Jerome ^{[1
]}

机构：

[1] Ecole Polytech Fed Lausanne, Lab Catalysis & Organ Synth, SB ISIC, BCH 4306, CH-1015 Lausanne, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 49期

关键词：

alkynes; C-H activation; gold catalysis; heterocycles; hypervalent iodine; H BOND FUNCTIONALIZATION; GACL3-CATALYZED ORTHO-ETHYNYLATION; CATALYZED DIRECT ALKYNYLATION; ROOM-TEMPERATURE; PALLADIUM; GOLD; ARYLATION; HYDROARYLATION; ALKYNES; TRIFLUOROMETHYLATION;

D O I：

10.1002/anie.200905419

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Chemical Equitation Presentation Easy does it: The unique properties of benziodoxolone alkynyl periodinane l and gold catalysts have allowed the development of a high yielding, operationally simple (room temperature, no dry sol-vents or inert conditions, commercially available catalyst) reaction for the introduction of silylacetylenes on a large range of indole and pyrrole heterocycles with a wide range of functional groups (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：9346 / 9349

页数：4

共 77 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] GaCl3-catalyzed ortho-ethynylation reaction of N-benzylanilines
Amemiya, R
Fujii, A
Yamaguchi, M
[J]. TETRAHEDRON LETTERS, 2004, 45 (22) : 4333 - 4335
[3] [Anonymous], 1990, PYRROLES
[4] [Anonymous], 2009, Angew. Chem., Int. Ed.
[5] [Anonymous], 2008, ANGEW CHEM INT EDIT
[6] [Anonymous], CHEM HETEROCYCLIC CO
[7] SYNTHESIS OF HIGHLY FUNCTIONALIZED BETA-LACTAMS - ALKYNYLATION OF 2-OXOAZETIDIN-1-YL MALONATES
BACHI, MD
BARNER, N
STANG, PJ
WILLIAMSON, BL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (27) : 7923 - 7924
[8] SYNTHESIS OF ALKYNYL(PHENYL)IODONIUM TRIFLATES AND THEIR REACTION WITH DIETHYL 2-AMINOMALONATE
BACHI, MD
BARNER, N
CRITTELL, CM
STANG, PJ
WILLIAMSON, BL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) : 3912 - 3915
[9] Palladium-catalysed cross-coupling and related reactions involving pyrroles
Banwell, Martin G.
Goodwin, Thomas E.
Ng, Sarah
Smith, Jason A.
Wong, David J.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (14) : 3043 - 3060
[10] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles
Beck, EM
Grimster, NP
Hatley, R
Gaunt, MJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2528 - 2529

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