Golden Route to Arene Compounds

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Science  24 Nov 2000:
Vol. 290, Issue 5496, pp. 1465
DOI: 10.1126/science.290.5496.1465d

Organic reactions catalyzed by gold compounds in solution are rather rare, but Hashmi et al. now report that highly substituted arenes, especially phenols, can be synthesized using gold catalysts. Either mixtures of allenyl and propargyl ketones, or, more conveniently, substituted furans possessing a terminal acetylene group, can form substituted phenols in the presence of AuCl3 with yields often exceeding 90%. The reaction can tolerate the presence of air and water and proceeds at room temperature. The authors suggest that gold activates the triple bond to form an oxygen-bridged six-membered ring through what would normally be an unfavorable Diels-Alder reaction with the furan. This oxygen bridge is broken by subsequent reaction with either a gold(I) or gold(III) species ultimately forming the phenol. — PDS

J. Am. Chem. Soc., in press.

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