Palladium-catalyzed Suzuki-Miyaura coupling reactions involving β,β-dihaloenamides:: Application to the synthesis of disubstituted ynamides

被引:47
作者
Couty, S [1 ]
Barbazanges, M [1 ]
Meyer, C [1 ]
Cossy, J [1 ]
机构
[1] Ecole Super Phys & Chim Ind Ville Paris, Assoc CNRS, Chim Organ Lab, F-75231 Paris, France
关键词
cross-coupling; palladium; enamides; eliminations; ynamides;
D O I
10.1055/s-2005-864821
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta,beta-Dihaloenamides can be successfully involved in palladium-catalyzed Suzuki-Miyaura coupling reactions. Whereas the resulting trisubstituted (Z)-beta-bromoenamides could participate in a second cross-coupling leading to beta, beta-disubstituted enamides, the (Z)-beta-chloroenamides have been converted to disubstituted ynamides by an E-2 elimination.
引用
收藏
页码:905 / 910
页数:6
相关论文
共 57 条
[1]   A STEREOSELECTIVE ROUTE TO 1-CHLORO-1-HALO-ENYNES, VERSATILE PRECURSORS FOR THE SYNTHESIS OF CHLOROENEDIYNES AND ENETRIYNES [J].
ALAMI, M ;
CROUSSE, B ;
LINSTRUMELLE, G .
TETRAHEDRON LETTERS, 1995, 36 (21) :3687-3690
[2]   Studies towards a postulated biomimetic Diels-Alder reaction for the synthesis of himgravine [J].
Baldwin, JE ;
Chesworth, R ;
Parker, JS ;
Russell, AT .
TETRAHEDRON LETTERS, 1995, 36 (52) :9551-9554
[3]   SYNTHESIS OF 2-FUNCTIONALIZED 1,1-DIIODO-1-ALKENES - GENERATION AND REACTIONS OF 1-IODO-1-LITHIO-1-ALKENES AND 1,1-DILITHIO-1-ALKENES [J].
BARLUENGA, J ;
RODRIGUEZ, MA ;
CAMPOS, PJ ;
ASENSIO, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) :5567-5568
[4]   Suzuki arylation of 1,1-dibromo-1-alkenes: Synthesis of tetra-substituted alkenes [J].
Bauer, A ;
Miller, MW ;
Vice, SF ;
McCombie, SW .
SYNLETT, 2001, (02) :254-256
[5]   Synthesis and determination of the absolute configuration of fugomycin and desoxyfugomycin:: CD spectroscopy and fungicidal activity of butenolides [J].
Braun, M ;
Hohmann, A ;
Rahematpura, J ;
Bühne, C ;
Grimme, S .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (18) :4584-4593
[6]  
Braun M, 2000, SYNLETT, P1070
[7]  
Brückner D, 2000, SYNLETT, P1402
[8]  
BryantFriedrich A, 1995, SYNTHESIS-STUTTGART, P1506
[9]   Iron-catalyzed coupling reaction between 1,1-dichloro-1-alkenes and Grignard reagents [J].
Dos Santos, M ;
Xavier, FA ;
Hocquemiller, R ;
Figadère, B ;
Peyrat, JF ;
Provot, O ;
Brion, JD ;
Alami, M .
SYNLETT, 2004, (15) :2697-2700
[10]   Copper-mediated N-alkynylation of carbamates, ureas, and sulfonamides. A general method for the synthesis of ynamides [J].
Dunetz, JR ;
Danheiser, RL .
ORGANIC LETTERS, 2003, 5 (21) :4011-4014