Recent advances on the synthetic applications of the dithioacetal functionality

Recent advances on the synthetic applications of the dithioacetal functionality are briefly reviewed. Nickel-catalyzed silylolefination reaction has led to the synthesis of a range of silyl-substituted olefins for optoelectronic interests. The reactions of propargylic dithioacetals with organocopper or lithium reagent followed by treatment with electrophiles yield the corresponding sulfur-substituted allenes. Further cross coupling with the Grignard reagent in the presence of a nickel catalyst affords highly substituted allenes. Acid-catalyzed cyclization of the sulfur-substituted allenyl alcohols furnishes a useful route for the synthesis of oligoaryls having highly substituted furan or pyrrole moieties. (C) 2002 Elsevier Science B.V. All rights reserved.