STUDY OF THE REGIOSELECTIVITY OF PALLADIUM-CATALYZED MONOCOUPLINGS BETWEEN CONJUGATED BIS(ENOLTRIFLATES) AND TRIMETHYLSILYLACETYLENE

Authors
MONIATTE M ECKHARDT M BRICKMANN K BRUCKNER R SUFFERT J
Citation
M. Moniatte et al., STUDY OF THE REGIOSELECTIVITY OF PALLADIUM-CATALYZED MONOCOUPLINGS BETWEEN CONJUGATED BIS(ENOLTRIFLATES) AND TRIMETHYLSILYLACETYLENE, Tetrahedron letters, 35(13), 1994, pp. 1965-1968
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
13
Year of publication
1994
Pages
1965 - 1968
Database
ISI
SICI code
0040-4039(1994)35:13<1965:SOTROP>2.0.ZU;2-J
Abstract
The Z-configurated bis(enoltriflates) 2 and 7 were treated at room tem perature with TMS acetylene (1.25 equiv.) in the presence of CuI (0. 1 7 equiv.) and various palladium catalysts (0.07 equiv.), solvents, and amines to afford monocoupling products. Surprisingly, opposite regios electivities were observed starting from the five-membered (-->8, n = 0) vs. the six-membered bis(enoltriflates) (-->9, n = 1).