Studies on the Synthesis of 2-Acyl-1H-Indenes via One-Pot Palladium-Catalysed Tandem Heck–Aldol Reaction

Abstract

2-Acyl-1H-indenes were synthesised efficiently by the reaction of o-halogenatedbenzaldehydes (or aryl ketones) with prop-2-en-1-ols via one-pot palladium-catalysed tandem Heck–aldol reaction in moderate to good yields. The optimal reaction conditions have been investigated and it was found that sodium acetate was the most effective base and in addition tetrabutylammonium chloride and LiCl was crucial for this process. Moreover, it was found that o-halogenatedbenzaldehydes react with various substituted prop-2-en-1-ols smoothly to produce the title compounds while 2-bromoacetophenone only reacted with 2-propen-1-ol to give the desired product.