Chain-Walking Strategy for Organic Synthesis: Catalytic Cycloisomerization of 1,n-Dienes
- 28 September 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 134 (40), 16544-16547
- https://doi.org/10.1021/ja308377u
Abstract
The catalytic construction of carbon-carbon bonds in small organic molecules via chain walking is described. Catalytic cycloisomerization of 1,n-dienes via chain walking was achieved using a palladium-1,10-phenanthroline catalyst to form five-membered-ring products. By means of a cycloisomerization/hydrogenation protocol, 1,7- to 1,14-dienes were selectively converted to bicyclo[4.3.0]nonane derivatives. The use of chain walking provides a new method in organic synthesis to functionalize unreactive carbon-hydrogen bonds by letting the catalyst look for preferable bond-forming sites by moving around on the substrate.Keywords
This publication has 31 references indexed in Scilit:
- Precise Isomerization Polymerization of Alkenylcyclohexanes: Stereoregular Polymers Containing Six-Membered Rings along the Polymer ChainJournal of the American Chemical Society, 2011
- Functionalization of Organic Molecules by Transition‐Metal‐Catalyzed C(sp3)-H ActivationChemistry – A European Journal, 2010
- Isomerization Polymerization of 4-Alkylcyclopentenes Catalyzed by Pd Complexes: Hydrocarbon Polymers with Isotactic-Type Stereochemistry and Liquid-Crystalline PropertiesJournal of the American Chemical Society, 2009
- Pd‐Catalyzed Polymerization of Dienes that Involves Chain‐Walking Isomerization of the Growing Polymer End: Synthesis of Polymers Composed of Polymethylene and Five‐Membered‐Ring UnitsAngewandte Chemie-International Edition, 2007
- Palladium-Catalyzed Alkylation of sp2 and sp3 C−H Bonds with Methylboroxine and Alkylboronic Acids: Two Distinct C−H Activation PathwaysJournal of the American Chemical Society, 2006
- Highly Regioselective Arylation of sp3 C−H Bonds Catalyzed by Palladium AcetateJournal of the American Chemical Society, 2005
- Thermal, Catalytic, Regiospecific Functionalization of AlkanesScience, 2000
- Chain Walking: A New Strategy to Control Polymer TopologyScience, 1999
- Copolymerization of Ethylene and Propylene with Functionalized Vinyl Monomers by Palladium(II) CatalystsJournal of the American Chemical Society, 1996
- New Pd(II)- and Ni(II)-Based Catalysts for Polymerization of Ethylene and .alpha.-OlefinsJournal of the American Chemical Society, 1995