Synthesis of carbobicyclic compounds via palladium-catalyzed cyclization/hydrosilylation: evidence for reversible silylpalladation.

Journal Article (Journal Article)

Cyclization/hydrosilylation of substituted 1-vinyl-1-(3-butenyl)cycloalkanes catalyzed by a 1:1 mixture of (phen)Pd(Me)Cl (1) and NaBAr(4) [phen = 1,10-phenanthroline; Ar = 3,5-C(6)H(3)(CF(3))(2)] formed silylated spirocycles in high yield with excellent regio and diastereoselectivity. Cyclization/hydrosilylation of substituted 3-(3-butenyl)cycloalkenes or 2,3-diallyl-5,6-dimethyl-1,4-hydroquinone diacetate (16) formed silylated fused bicyclic complexes in good yield. Reaction of substituted 1,6,11-nonatrienes with silane catalyzed by 1/NaBAr(4) led to cascade cyclization with hydrosilylation. This latter procedure was employed in the synthesis of silylated bicyclopentanes and a linear triquinane.

Full Text

Duke Authors

Cited Authors

  • Wang, X; Chakrapani, H; Stengone, CN; Widenhoefer, RA

Published Date

  • March 2001

Published In

Volume / Issue

  • 66 / 5

Start / End Page

  • 1755 - 1760

PubMed ID

  • 11262123

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo001438k


  • eng