Carbonylative cross-coupling reaction of ethynylstibane with aryl iodides.
Palladium-catalyzed carbonylative cross-coupling reaction of ethynylstibane (PhSbPh(2)) and aryl iodides (Ar-I) is described. The reaction of the stibanes and the halides under 1 atm of carbon monoxide in N,N-dimethylacetamide using a combination of 5 mol% Pd(OAc)(2) and 4 equivalents (20 mol%) of PPh(3) brought about carbonylative cross-coupling reaction to afford arylethynylketones [ArC(O)Ph] in good yields along with a small amount of directly coupled products, aryl acetylens (ArPh). Formation of the side product was completely suppressed by conducting the reaction under high CO pressure (20 atm) conditions. The present method provides a variety of carbonylated products in good yield even with electron-deficient aryl iodides which usually give inferior results due to their tendency to undergo decarbonylation in the cross-coupling reaction of ethynylstibanes and acyl halides.
Kakusawa
Naoki
N
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan.
Kurita
Jyoji
J
D000480:Alkynes / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium; D012997:Solvents
D000480:Alkynes; D006847:Hydrocarbons, Iodinated; D009942:Organometallic Compounds; D012997:Solvents; C511394:ethynylstibane; D010165:Palladium; D002248:Carbon Monoxide