Sonogashira cross-couplings of ynamides. Syntheses of urethane- and sulfonamide-terminated conjugated phenylacetylenic systems

被引:62
作者
Tracey, MR [1 ]
Zhang, YS [1 ]
Frederick, MO [1 ]
Mulder, JA [1 ]
Hsung, RP [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol0493251
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first successful Sonogashira coupling of ynamides with aryl and vinyl iodides is described here. This study resolves the problem of the competing pathway involving homocoupling of ynamides and provides a practical entry to novel urethane- or sulfonamide-terminated conjugated acetylenic systems. An interesting tandem hydrohalogenation and Sonogashira coupling was also observed to give an en-ynamide.
引用
收藏
页码:2209 / 2212
页数:4
相关论文
共 53 条
[1]   Single electron electronics: Challenge for nanofabrication [J].
Ahmed, H .
JOURNAL OF VACUUM SCIENCE & TECHNOLOGY B, 1997, 15 (06) :2101-2108
[2]  
Cadiot P., 1969, Chemistry of Acetylenes, P597
[3]  
Collman J.P., 1987, PRINCIPLES APPL ORGA
[4]   Self-assembly of conjugated molecular rods: A high-resolution STM study [J].
Dhirani, AA ;
Zehner, RW ;
Hsung, RP ;
GuyotSionnest, P ;
Sita, LR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (13) :3319-3320
[5]   SYNTHESIS, STRUCTURE, AND PROPERTIES OF MODEL ORGANIC-SURFACES [J].
DUBOIS, LH ;
NUZZO, RG .
ANNUAL REVIEW OF PHYSICAL CHEMISTRY, 1992, 43 :437-463
[6]   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
[7]   Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols [J].
Frederick, MO ;
Hsung, RP ;
Lambeth, RH ;
Mulder, JA ;
Tracey, MR .
ORGANIC LETTERS, 2003, 5 (15) :2663-2666
[8]   A copper-catalyzed C-N bond formation involving sp-hybridized carbons. A direct entry to chiral ynamides via N-alkynylation of amides [J].
Frederick, MO ;
Mulder, JA ;
Tracey, MR ;
Hsung, RP ;
Huang, J ;
Kurtz, KCM ;
Shen, LC ;
Douglas, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2368-2369
[9]  
Glaser C, 1869, CHEM GES, V2, P422
[10]   Practical preparation of N-(1-alkynyl)sulfonamides and their remote diastereoselective addition to aldehydes via titanation [J].
Hirano, S ;
Tanaka, R ;
Urabe, H ;
Sato, F .
ORGANIC LETTERS, 2004, 6 (05) :727-729