Ruthenium-Catalyzed Regioselective 1,3-Methylene Transfer by Cleavage of Two Adjacent σ-Carbon−Carbon Bonds: An Easy and Selective Synthesis of Highly Subsituted Benzenes
- 1 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (12) , 4186-4187
- https://doi.org/10.1021/ja0504901
Abstract
We report a new ruthenium-catalyzed 6-endo-dig cyclization of 6,6-cycloalkylidenyl-3,5-dien-1-ynes, which produces highly substituted benzenes with considerable structural reorganization. In this process, we observe a regioselective 1,3-methylene migration via extrusion from a cycloalkylidenyl ring, in addition to a regiocontrolled 1,2-alkyl migration. This cyclization provides an easy and convenient synthesis of complex benzenes bearing various different substituents.Keywords
This publication has 14 references indexed in Scilit:
- Rutheniun-Catalyzed Cycloisomerization of o-(Ethynyl)phenylalkenes to Diene Derivatives via Skeletal RearrangementJournal of the American Chemical Society, 2004
- Nickel-Catalyzed Arylcyanation of AlkynesJournal of the American Chemical Society, 2004
- Ruthenium-Catalyzed Aromatization of Aromatic Enynes via the 1,2-Migration of Halo and Aryl Groups: A New Process Involving Electrocyclization and Skeletal RearrangementJournal of the American Chemical Society, 2003
- Palladium-Catalyzed Asymmetric Arylation, Vinylation, and Allenylation of tert-Cyclobutanols via Enantioselective C−C Bond CleavageJournal of the American Chemical Society, 2003
- The Behavior of 1,n-Enynes in the Presence of Transition MetalsChemical Reviews, 2002
- Reactions of Iodinated Vinylidene Complexes Generated from 1-Iodo-1-alkynes and W(CO)5(thf)Journal of the American Chemical Society, 2002
- Metal Insertion into C−C Bonds in SolutionAngewandte Chemie International Edition in English, 1999
- PtCl2-Catalyzed Conversion of 1,6- and 1,7-Enynes to 1-Vinylcycloalkenes. Anomalous Bond Connection in Skeletal Reorganization of EnynesOrganometallics, 1996
- Theoretical studies of [1,n]-sigmatropic rearrangements involving hydrogen transfer in simple methyl-substituted conjugated polyenesJournal of the American Chemical Society, 1985
- An MC-SCF study of [1,3] and [1,2] sigmatropic shifts in propeneJournal of the American Chemical Society, 1984