General and efficient indole syntheses based on catalytic amination reactions

被引：186

作者：

Ackermann, L ^{[1
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 03期

关键词：

D O I：

10.1021/ol047649j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly flexible and efficient syntheses of the indole backbone are presented starting from o-alkynylhaloarenes. These transformations proceed via a palladium- or a copper-catalyzed amination reaction and a subsequent cyclization reaction in good to excellent yields. Furthermore. a multicatalytic one-pot indole synthesis starting from o-chloroiodobenzene is viable using a single catalyst consisting of an N-heterocyclic carbene palladium complex and Cul.

引用

页码：439 / 442

页数：4

共 35 条

[1] Hydroamination/Heck reaction sequence for a highly regioselective one-pot synthesis of indoles using 2-chloroaniline
Ackermann, L
Kaspar, LT
Gschrei, CJ
[J]. CHEMICAL COMMUNICATIONS, 2004, (24) : 2824 - 2825
[2] PALLADIUM-CATALYZED COUPLING OF ARYL AND VINYL TRIFLATES OR HALIDES WITH 2-ETHYNYLANILINE - AN EFFICIENT ROUTE TO FUNCTIONALIZED 2-SUBSTITUTED INDOLES
ARCADI, A
CACCHI, S
MARINELLI, F
[J]. TETRAHEDRON LETTERS, 1989, 30 (19) : 2581 - 2584
[3] IPy2BF4-promoted intramolecular addition of masked and unmasked anilines to alkynes:: Direct assembly of 3-iodoindole cores
Barluenga, J
Trincado, M
Rubio, E
González, JM
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (21) : 2406 - 2409
[4] Synthesis of 2,3-dihydroindoles, indoles, and anilines by transition metal-free amination of aryl chlorides
Beller, M
Breindl, C
Riermeier, TH
Tillack, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) : 1403 - 1412
[5] PALLADIUM-CATALYZED CYCLIZATION OF 2-ALKYNYLANILINES TO 2-SUBSTITUTED INDOLES UNDER AN ACIDIC 2-PHASE SYSTEM
CACCHI, S
CARNICELLI, V
MARINELLI, F
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 475 (1-2) : 289 - 296
[6] INDOLES BENZOFURANS PHTHALIDES AND TOLANES VIA COPPER(1) ACETYLIDES
CASTRO, CE
GAUGHAN, EJ
OWSLEY, DC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) : 4071 - +
[7] Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones
Chen, CY
Lieberman, DR
Larsen, RD
Verhoeven, TR
Reider, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) : 2676 - 2677
[8] Gilchrist Thomas Lonsdale, 1997, Heterocyclic Chemistry
[9] HARTWIG JF, 2000, MODERN AMINATION MET, P195
[10] Development of an efficient procedure for indole ring synthesis from 2-ethynylaniline derivatives catalyzed by Cu(II) salts and its application to natural product synthesis
Hiroya, K
Itoh, S
Sakamoto, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) : 1126 - 1136

← 1 2 3 4 →