Rhodium-Catalyzed Allylic Substitution Reactions with Indium(III) Organometallics

被引:12
作者
Riveiros, Ricardo [1 ]
Tato, Ruben [1 ]
Perez Sestelo, Jose [1 ]
Sarandeses, Luis A. [1 ]
机构
[1] Univ A Coruna, Dept Quim Fundamental, La Coruna 15071, Spain
关键词
Organometallics; Indium; Rhodium; Allylic compounds; C-C coupling; CROSS-COUPLING REACTIONS; TRIORGANOINDIUM REAGENTS; PALLADIUM; ALKYLATION; ARYL; HALIDES; CARBONATES; COMPLEXES; ARYLATION; ALCOHOLS;
D O I
10.1002/ejoc.201200104
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel rhodium-catalyzed allylic substitution reaction using indium organometallics is reported. Aryl- and heteroarylindium reagents reacted in THF at 80 degrees C with primary and secondary allyl halides and their derivatives under rhodium(I) catalysis to afford the a-substituted products in good yields and with high regio- and stereoselectivity. The reaction takes place with substoichiometric amounts of the triorganoindium reagents, which demonstrates the efficiency of the indiumrhodium transmetallation process in carboncarbon bond-forming reactions.
引用
收藏
页码:3018 / 3023
页数:6
相关论文
共 73 条
[11]   Enantiospecific and regioselective rhodium-catalyzed allylic alkylation: Diastereoselective approach to quaternary carbon stereogenic centers [J].
Evans, PA ;
Kennedy, LJ .
ORGANIC LETTERS, 2000, 2 (15) :2213-2215
[12]   Regioselective rhodium-catalyzed allylic alkylation with a modified Wilkinson's catalyst [J].
Evans, PA ;
Nelson, JD .
TETRAHEDRON LETTERS, 1998, 39 (13) :1725-1728
[13]   Regioselective rhodium-catalyzed allylic linchpin cross-coupling reactions:: Diastereospecific construction of anti-1,3-carbon stereogenic centers and C2-symmetrical fragments [J].
Evans, PA ;
Kennedy, LJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (06) :1234-1235
[14]   Regio- and diastereoselective tandem rhodium-catalyzed allylic alkylation Pauson-Khand annulation reactions [J].
Evans, PA ;
Robinson, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (19) :4609-4610
[15]   Palladium-catalyzed coupling of thiol esters with aryl and primary and secondary alkyl organoindium reagents [J].
Fausett, BW ;
Liebeskind, LS .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (12) :4851-4853
[16]   Indium-mediated synthesis of heterobiaryls [J].
Font-Sanchis, Enrique ;
Cespedes-Guirao, F. Javier ;
Sastre-Santos, Angela ;
Fernandez-Lazaro, Fernando .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (09) :3589-3591
[17]   A new convergent strategy for the synthesis of calixarenes via a triple annulation of Fischer carbene complexes [J].
Gopalsamuthiram, V ;
Wulff, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (43) :13936-13937
[18]   High enantioselectivity in rhodium-catalyzed allylic alkylation of 1-substituted 2-propenyl acetates [J].
Hayashi, T ;
Okada, A ;
Suzuka, T ;
Kawatsura, M .
ORGANIC LETTERS, 2003, 5 (10) :1713-1715
[19]   STRUCTURAL EFFECTS ON RATES AND EQUILIBRA .22. TERT-BUTOXY AND 2-FURYL - 2 EFFECTIVE SUBSTITUENTS AT STABILIZING CARBON-CARBON DOUBLE-BONDS [J].
HINE, J ;
LINDEN, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (08) :1635-1638
[20]  
Hoveyda A. H., 1999, COMPREHENSIVE ASYMME, P431