Regioselective Pd-catalyzed indolization of 2-bromoanilines with internal alkynes using phosphine-free ligands

被引：49

作者：

Cui, Xin ^{[1
]}

Li, Juan ^{[1
]}

Fu, Yao ^{[1
]}

Liu, Lei ^{[1
,2
]}

Guo, Qing-Xiang ^{[1
]}

机构：

[1] Univ Sci & Technol China, Joint Lab Green Synthet Chem, Dept Chem, Hefei 230026, Peoples R China

[2] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 21期

基金：

中国国家自然科学基金;

关键词：

indole; Larock indolization; palladium catalyst; phosphine-free ligand; heteroannulation;

D O I：

10.1016/j.tetlet.2008.03.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The possibility of using phosphine-free ligands to promote Pd-catalyzed indolization of 2-bromoanilines with internal alkynes was examined for the first time. Phenylurea was found to be the optimal ligand, which could mediate the synthesis of 2,3 -disubstituted indoles in good yields (ca. 60-85%) with high regioselectivity. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3458 / 3462

页数：5

共 69 条

[1] General and efficient indole syntheses based on catalytic amination reactions [J].

Ackermann, L .

ORGANIC LETTERS, 2005, 7 (03) :439-442

[2] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[3] Access to well-defined heterogeneous catalytic systems via ring-opening metathesis polymerization (ROMP): Applications in palladium(II)-mediated coupling reactions [J].

Buchmeiser, MR ;

Wurst, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11101-11107

[4] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) :7421-7426

[5] A facile synthesis of various fluorine-containing indole derivatives via palladium-catalyzed annulation of internal alkynes [J].

Chae, J ;

Konno, T ;

Ishihara, T ;

Yamanaka, H .

CHEMISTRY LETTERS, 2004, 33 (03) :314-315

[6] Synthesis of indoles: Efficient functionalisation of the 7-position [J].

Charrier, Nicolas ;

Demont, Emmanuel ;

Dunsdon, Rachel ;

Maile, Graham ;

Naylor, Alan ;

O'Brien, Alistair ;

Redshaw, Sally ;

Theobald, Pam ;

Vesey, David ;

Walter, Daryl .

SYNTHESIS-STUTTGART, 2006, (20) :3467-3477

[7]

CHEN J, 2006, ORG CHEM, V26, P996

[8] The design and synthesis of bis(thiourea) ligands and their application in Pd-catalyzed Heck and Suzuki reactions under aerobic conditions [J].

Chen, W ;

Li, R ;

Han, B ;

Li, BJ ;

Chen, YC ;

Wu, Y ;

Ding, LS ;

Yang, D .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (05) :1177-1184

[9] Highly active Pd(II) catalysts with pyridylbenzoimidazole ligands for the Heck reaction [J].

Chen, Weixuan ;

Xi, Chanjuan ;

Wu, Yongwei .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (20) :4381-4388

[10] An example of regioselective Fischer indole annulation [J].

Christoffers, J .

SYNLETT, 2006, (02) :318-320

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