InBr3 as a versatile and highly efficient catalyst for the synthesis of 3-allyl- and 3-benzylindoles

被引:42
作者
Yadav, J. S. [1 ]
Reddy, B. V. Subba [1 ]
Aravind, S. [1 ]
Kumar, G. G. K. S. Narayana [1 ]
Reddy, A. Srinivas [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
indium reagents; benzylic/allylic alcohols; indoles; benzylation; allylation;
D O I
10.1016/j.tetlet.2007.06.144
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Indoles undergo smooth alkylation with allylic and benzylic alcohols in the presence of 10 mol % of InBr3 under mild conditions to produce 3-allyl- and 3-benzyl indoles, respectively, in excellent yields and with high selectivity. This is the first example of the alkylation of indoles with benzylic alcohols using InBr3 as an acid catalyst. (c) 2007 Published by Elsevier Ltd.
引用
收藏
页码:6117 / 6120
页数:4
相关论文
共 35 条
[1]   New versatile route to the synthesis of tetrahydro-β-carbolines and tetrahydro-pyrano[3,4-b]indoles via an intramolecular Michael addition catalyzed by InBr3 [J].
Agnusdei, M ;
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7126-7129
[2]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[3]   A journey across recent advances in catalytic and stereoselective alkylation of indoles [J].
Bandini, M ;
Melloni, A ;
Tommasi, S ;
Umani-Ronchi, A .
SYNLETT, 2005, (08) :1199-1222
[4]   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
[5]   New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].
Bandini, M ;
Melloni, A ;
Umani-Ronchi, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556
[6]   The Michael addition of indoles to α,β-unsaturated ketones catalyzed by CeCl3•7H2O-NaI combination supported on silica gel [J].
Bartoli, G ;
Bartolacci, M ;
Bosco, M ;
Foglia, G ;
Giuliani, A ;
Marcantoni, E ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4594-4597
[7]   Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].
Cacchi, S ;
Fabrizi, G .
CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920
[8]   Benzylic substitution of gramines with boronic acids and rhodium or iridium catalysts [J].
de la Herran, Gabriela ;
Segura, Amaya ;
Csaky, Aurelio G. .
ORGANIC LETTERS, 2007, 9 (06) :961-964
[9]   Marine natural products [J].
Faulkner, DJ .
NATURAL PRODUCT REPORTS, 2001, 18 (01) :1-49
[10]   Synthesis of aromatic heterocycles [J].
Gilchrist, TL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (20) :2491-2515