Palladium-Catalyzed C3-Benzylation of Indoles

被引:128
作者
Zhu, Ye [1 ]
Rawal, Viresh H. [1 ]
机构
[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
基金
美国国家卫生研究院;
关键词
2,3-DISUBSTITUTED INDOLES; FUNCTIONALIZATION; DERIVATIVES; ALKYLATION; ALLYLATION; HYDROAMINATION; SUBSTITUTION; BENZYLATION; VINYLARENES; OXINDOLES;
D O I
10.1021/ja2095393
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A general method for regioselective C3-benzylation of indoles has been developed. Various 3-substituted indoles and benzyl methyl carbonates with different electronic properties react under mild conditions to afford a diverse range of 3-benzylindolenine products in good yields.
引用
收藏
页码:111 / 114
页数:4
相关论文
共 42 条
[1]   Highly enantioselective synthesis of tetrahydro-β-carbolines and tetrahydro-γ-carbolines via Pd-catalyzed intramolecular allylic alkylation [J].
Bandini, M ;
Melloni, A ;
Piccinelli, F ;
Sinisi, R ;
Tommasi, S ;
Umani-Ronchi, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1424-1425
[2]   New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic subsitution: Controlling the regioselectivity [J].
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
ORGANIC LETTERS, 2004, 6 (18) :3199-3202
[3]   Catalytic Functionalization of Indoles in a New Dimension [J].
Bandini, Marco ;
Eichholzer, Astrid .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) :9608-9644
[4]   Organocatalytic strategies for the asymmetric functionalization of indoles [J].
Bartoli, Giuseppe ;
Bencivenni, Giorgio ;
Dalpozzo, Renato .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) :4449-4465
[5]   DYNAMIC ETA-1-BENZYLBIS(TRIETHYLPHOSPHINE) AND ETA-3-BENZYLBIS(TRIETHYLPHOSPHINE)PALLADIUM(II) CATIONS - MECHANISMS OF INTERCONVERSION [J].
BECKER, Y ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (03) :845-850
[6]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[7]   Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions [J].
Cacchi, Sandro ;
Fabrizi, Giancarlo .
CHEMICAL REVIEWS, 2011, 111 :PR215-PR283
[8]   NMR-SPEKTROSKOPISCHE UNTERSUCHUNG DER RAUMLICHEN STRUKTUR UND DER DISSOZIATION DES TRIMEREN BETA.BETA-DIMETHYL-INDOLENINS [J].
FRITZ, H ;
PFAENDER, P .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (03) :989-&
[9]   Enantioselective total synthesis of aspidophytine [J].
He, F ;
Bo, YX ;
Altom, JD ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (28) :6771-6772
[10]  
Hoshino T, 1933, LIEBIGS ANN CHEM, V500, P35