Saturday, April 28, 2007

Rhodium-Catalyzed Arylative and Alkenylative Cyclization of 1,5-Enynes Induced by Geminal Carbometalation of Alkynes


Yiyun Chen and Chulbom Lee
J. Am. Chem. Soc.,
2006, 128, 15598 -15599
DOI: 10.1021/ja067125+

Summary: A Rh(I)-catalyzed alkyne-boronic acid addition-cyclization has been developed to afford various alkenyl ketone derivatives. The reaction is believed to proceed through a metal vinylidene complex which eventually undergoes an intramolecular conjugate addition to provide the desired cyclized ketone adduct.


10 examples : Reaction Optimization (0-65% yield)
19 examples: Reaction Scope (11-84% yield)
2 examples: Deuterated substrates for mechanistic studies