Abstract
Rhodium-catalyzed carbonylation of acetylenes was studied. Under water-gas shift reaction conditions, internal acetylenes are selectively carbonylated to 3,4-disubstituted furan-2(5H)-ones (2). Use of D 2 O gave 5,5-dideuteriofuran-2(5H)-one (3), which indicates that the hydrogen comes from water. Use of molecular hydrogen in place of water gave hydroxymethylated product 4 and stilbene 5, and no furanone was obtained, indicating that water-gas shift reaction conditions are indespensable for the formation of furanones. As catalysts, rhodium carbonyl clusters such as Rh 4 (CO) 12 and Rh 6 (CO) 16 are the best among the transition-metal complexes tested. The presence of amines is essential for the selective synthesis of furanones. Effects of additives, solvents, and the pressure of carbon monoxide were examined
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