Chemoselective and metal-free reduction of alpha,beta-unsaturated ketones byin situproduced benzeneselenol fromO-(tert-butyl) Se-phenyl selenocarbonate

摘要

The carbon-carbon double bond of arylidene acetones and chalcones can be selectively reduced with benzeneselenol generatedin situby reactingO-(tert-butyl) Se-phenyl selenocarbonate with hydrochloric acid in ethanol. This mild, metal-free and experimentally simple reduction procedure displays considerable functional-group compatibility, products are obtained in good to excellent yields, and the use of toxic Se/CO mixture and NaSeH, or the smelly and air-sensitive benzeneselenol, is avoided.