Palladium pincer-complex catalyzed allylation of tosylimines by potassium trifluoro(allyl)borates

被引:100
作者
Solin, N [1 ]
Wallner, OA [1 ]
Szabó, KJ [1 ]
机构
[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, SE-10691 Stockholm, Sweden
关键词
D O I
10.1021/ol0475010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium pincer complex 1 catalyzes the reaction of trifluoro(allyl)borate 2 with a wide range of tosylimines (3) under mild and neutral reaction conditions. This catalytic transformation affords homoallylic annines (4) in good to excellent yield. Mechanistic studies suggest that a transmetalation reaction between complex 1 and the borate salt 2 provides an eta(1)-allyipalladium complex, which subsequently reacts with the imine substrate.
引用
收藏
页码:689 / 691
页数:3
相关论文
共 28 条
[1]   Potassium allyl- and crotyltrifluoroborates: Stable and efficient agents for allylation and crotylation [J].
Batey, RA ;
Thadani, AN ;
Smil, DV .
TETRAHEDRON LETTERS, 1999, 40 (23) :4289-4292
[2]  
Batey RA, 2000, SYNTHESIS-STUTTGART, P990
[3]   Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].
Darses, S ;
Genet, JP .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327
[4]  
Farina V., 1997, ORG REACT, V50, P1, DOI DOI 10.1002/0471264180.or050.01
[5]   Chiral bis-π-allylpalladium complex catalyzed asymmetric allylation of imines:: Enhancement of the enantioselectivity and chemical yield in the presence of water [J].
Fernandes, RA ;
Stimac, A ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) :14133-14139
[6]  
Hegedus L.S., 1999, TRANSITION METALS SY, V2nd
[7]   Mechanistic studies on Pd-catalyzed telomerization and co-cyclization of butadiene:: Amphiphilicity of bis-π-allylpalladium intermediate in the presence of phosphine ligand [J].
Kiji, J ;
Okano, T ;
Nomura, T ;
Saiki, K ;
Sai, T ;
Tsuji, J .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (10) :1939-1945
[8]   Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates [J].
Molander, GA ;
Biolatto, B .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4302-4314
[9]   Catalytic amphiphilic allylation via bis-π-allylpalladium complexes and its application to the synthesis of medium-sized carbocycles [J].
Nakamura, H ;
Aoyagi, K ;
Shim, JG ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (03) :372-377
[10]   Amphiphilic catalytic allylating reagent, bis-pi-allylpalladium complex [J].
Nakamura, H ;
Shim, JG ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (34) :8113-8114