1218903-69-5Relevant articles and documents
Rhodium-catalyzed convenient synthesis of functionalized tetrahydronaphthalenes
Tanaka, Ken,Sawada, Yayoi,Aida, Yusuke,Thammathevo, Maliny,Tanaka, Rie,Sagae, Hiromi,Otake, Yousuke
experimental part, p. 1563 - 1569 (2010/04/06)
Convenient as well as convergent synthesis of functionalized tetrahydronaphthalenes has been accomplished under mild reaction conditions by the cationic rhodium(I)/H8-BINAP complex-catalyzed [2+2+2] cycloaddition of 1,7-octadiyne derivatives with functionalized monoynes. The effect of the diyne tether lengths was investigated, which revealed that 1,6-heptadiyne and 1,7-octadiyne exhibit higher reactivity than 1,8-nonadiyne. Mechanistic studies indicated that the present rhodium-catalyzed [2+2+2] cycloaddition proceeds through the rhodacyclopentadiene intermediate generated by oxidative coupling of a diyne with rhodium. On the other hand, in the reactions of diynes and dimethyl acetylenedicarboxylate, the rhodacyclopentadiene intermediate generated by oxidative coupling of a diyne and a monoyne with rhodium would also be involved.
