title: Rhodium(I)-catalyzed cycloisomerization of benzylallene-alkynes through C-H activation.
abstract: The efficient Rh(I)-catalyzed cycloisomerization of benzylallene-alkynes produced the tricyclo[9.4.0.0(3,8)]pentadecapentaene skeleton through a C(sp2)-H bond activation in good yields. A plausible reaction mechanism proceeds via oxidative addition of the acetylenic C-H bond to Rh(I), an ene-type cyclization to the vinylidenecarbene-Rh(I) intermediate, and an electrophilic aromatic substitution with the vinylidenecarbene species. It was proposed based on deuteration and competition experiments.
authors.affiliation: Division of Pharmaceutical Sciences, Graduate School of Medicinal Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192 (Japan).
authors.forename: Yasuaki
authors.initials: Y
authors.lastname: Kawaguchi
authors.forename: Shigeo
authors.initials: S
authors.lastname: Yasuda
authors.forename: Akira
authors.initials: A
authors.lastname: Kaneko
authors.forename: Yuki
authors.initials: Y
authors.lastname: Oura
authors.forename: Chisato
authors.initials: C
authors.lastname: Mukai
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007536:Isomerism; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D000480:Alkynes; C025947:propadiene; D012238:Rhodium
keywords: C-H activation; alkynes; allenes; cycloisomerization; rhodium