Synthesis p. 746 - 748 (1992)
Update date:2022-08-04
Topics: Column chromatography Yield NMR spectroscopy Ligand TLC (thin-layer chromatography) Workup Base Oxidative Addition Reductive Elimination Reaction Time Catalyst Loading Transmetalation Sonogashira Coupling Aryl Iodides Terminal Alkyne Inert atmosphere Palladium-Catalyzed Cross-Coupling Reaction Schlenk technique Solvent system
Sakamoto
Shiga
Yasuhara
Uchiyama
Kondo
Yamanaka
The palladium-catalyzed cross-coupling reaction of aryl iodides with 3,3,3-triethoxy-1-propyne gave 1-aryl-3,3,3-triethoxy-1-propynes which were converted to the corresponding ethyl arylpropiolates. The arylpropiolates were also synthesized from the cross-coupling reactions of aryl iodides with 2-ethoxycarbonyl-1-ethynylzinc chloride or ethyl (tributylstannyl)propiolate, but the reactions were not generally applicable.
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Doi:10.1021/jo00339a035
(1981)Doi:10.1021/jo00090a040
(1994)Doi:10.1248/cpb.38.19
(1990)Doi:10.1007/BF00955304
(1981)Doi:10.1021/ic049154w
(2004)Doi:10.1021/ja0458827
(2004)
