Web Release Date: October 11,
Nickel(0)-Catalyzed [2 + 2 + 2 + 2] Cycloadditions of Terminal Diynes for the Synthesis of Substituted Cyclooctatetraenes
Departments of Chemistry and Chemical and Systems Biology, Stanford University, Stanford, California 94305-5080
Received August 21, 2007
Abstract:
The Ni(0)-catalyzed [2 + 2 + 2 + 2] cycloadditions of 1,6- and 1,7-diynes are shown to provide an efficient and selective method for the preparation of 1,2,5,6-tetrasubstituted cyclooctatetraenes (COTs). Catalysts and conditions are described that favor in all cases COT formation over competing [2 + 2 + 2] cycloadditions. A hitherto unexplored crossed reaction is also described, providing access to non-symmetrical COTs.
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