New synthetic reactions using group 11 metal compounds as a catalyst

This article presents several synthetic reactions by using a catalyst conta ining group 11 metals. We recently found an unprecedented reaction between an alkynylsilane and CuCl to produce the corresponding alkynylcopper(I) in DMI (1,3-dimethyl-2-imidazolidinone). This transformation was applied to th e synthesis of alkynyl ketones catalyzed by CuCl. A new and convenient proc edure for the stereo- and chemoselective reduction of carbonyl compounds by use of a complex of copper(I) hydride generated from a hydrosilane and a c opper(I) salt is described. A new method for the synthesis of enol esters ( O-acylated products) from silyl enol ethers by use of a copper(I) salt is a lso described. An unprecedented cleavage reaction of the silicon-silicon bo nd in a disilane with a Cu(I) salt and its new 1,4-addition reaction toward alpha,beta-unsaturated carbonyl compounds in the presence of a catalytic a mount of a Cu(I) salt is reported. Thus under these conditions, organosilyl -, hydrido-, alkynyl-, aryl- and heteroarylsilanes were smoothly converted to the corresponding organocopper reagents. Similarly, Au(I) complexes effi ciently catalyze the dehydrogenative dimerization of trialkylstannanes and hydrosilylation of aldehydes. The present method provides new synthetic too ls.