C-H bond functionalizations with palladium(II): intramolecular oxidative annulations of arenes

被引：119

作者：

Ferreira, Eric M. ^{[1
]}

Zhang, Haiming ^{[1
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 26期

关键词：

D O I：

10.1016/j.tet.2008.01.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative annulations for the synthesis of carbocycles were developed using a catalytic palladium(II) system. Indoles with pendant olefin tethers were oxidatively cyclized to form annulated products. Electron-rich aromatic systems were also investigated, culminating in the synthesis of benzofurans and dihydrobenzofurans by a similar protocol. These reactions were demonstrated to proceed by an initial C-H bond functionalization event, followed by olefin insertion and beta-hydride elimination. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5987 / 6001

页数：15

共 73 条

[41] KUNAPULI SP, 1981, J INDIAN I SCI C-BIO, V63, P167
[42] LINK JT, 2002, ORG REACTIONS, V60, P157, DOI DOI 10.1002/0471264180.0R060.02
[43] Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins
Liu, C
Han, XQ
Wang, X
Widenhoefer, RA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) : 3700 - 3701
[44] Mikami K, 1999, CHEM LETT, P55
[45] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
MIYAURA, N
SUZUKI, A
[J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483
[46] Negishi E., 2002, HDB ORGANOPALLADIUM
[47] Palladium(II)-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen
Nishimura, T
Onoue, T
Ohe, K
Uemura, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) : 6750 - 6755
[48] Perrin D. D., 1965, DISSOCIATION CONSTAN, P141
[49] RAMSEY BG, **NON-TRADITIONAL**
[50] Ru-, Rh-, and Pd-catalyzed C-C bond formation involving C-H activation and addition on unsaturated substrates: Reactions and mechanistic aspects
Ritleng, V
Sirlin, C
Pfeffer, M
[J]. CHEMICAL REVIEWS, 2002, 102 (05) : 1731 - 1769

← 1 2 3 4 5 6 7 8 →