Oxazolinethiones and oxazolidinethiones for the first copper-catalyzed desulfurative cross-coupling reaction and first Sonogashira applications

被引:61
作者
Silva, Sandrina [1 ,2 ]
Sylla, Balla [1 ]
Suzenet, Franck [1 ]
Tatibouet, Arnaud [1 ]
Rauter, Amelia P. [2 ]
Rollin, Patrick [1 ]
机构
[1] Univ Orleans, CNRS UMR 6005, Inst Chim Organ & Anal, F-45067 Orleans, France
[2] Univ Lisbon, Fac Ciencias, Dept Quim & Bioquim, P-1749016 Lisbon, Portugal
关键词
D O I
10.1021/ol703003e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cyclic thionocarbamates, namely chiral oxazolidinethiones (OZT) and aromatic oxazolinethiones (OXT), were involved, for the first time, in Sonogashira cross-coupling. A cooperative effect of two different copper (1) species-Cul and CuTC-accounts for this new copper-catalyzed desulfurative carbon-carbon cross-coupling reaction. This cooperative reactivity could also be extended to other copper (I) catalysts.
引用
收藏
页码:853 / 856
页数:4
相关论文
共 39 条
[1]   Pd-catalyzed, cu(I)-mediated cross-couplings of bisarylthiocyclobutenediones with boronic acids and organostannanes [J].
Aguilar-Aguilar, Angelica ;
Liebeskind, Lanny S. ;
Pena-Cabrera, Eduardo .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8539-8542
[2]   Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].
Alphonse, FA ;
Suzenet, F ;
Keromnes, A ;
Lebret, B ;
Guillaumet, G .
ORGANIC LETTERS, 2003, 5 (06) :803-805
[3]  
Alphonse FA, 2002, SYNLETT, P447
[4]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[5]   Synthesis and evaluation of novel oxazoline MMP inhibitors [J].
Cook, GR ;
Manivannan, E ;
Underdahl, T ;
Lukacova, V ;
Zhang, YF ;
Balaz, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (19) :4935-4939
[6]  
de Meijere A., 2004, METAL CATALYZED CROS, V1
[7]   REACTIVITY OF BETA-AMINO ALCOHOLS WITH CARBON-DISULFIDE - STUDY ON THE SYNTHESIS OF 2-OXAZOLIDINETHIONES AND 2-THIAZOLIDINETHIONES [J].
DELAUNAY, D ;
TOUPET, L ;
LECORRE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (20) :6604-6607
[8]   Sugar-based ethenyl ethers:: stereoselective dipolar cycloadditions of nitrile oxides [J].
Desroses, M ;
Chéry, F ;
Tatibouët, A ;
De Lucchi, O ;
Rollin, P .
TETRAHEDRON-ASYMMETRY, 2002, 13 (23) :2535-2539
[9]   Organosulfur compounds: Electrophilic reagents in transition-metal-catalyzed carbon-carbon bond-forming reactions [J].
Dubbaka, SR ;
Vogel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (47) :7674-7684
[10]  
FERNANDEZ JMG, 1993, J ORG CHEM, V58, P5192