Abstract
An environmentally-friendly, enzyme-promoted procedure for the Henry reaction was first studied using water-in-[Bmim][PF6] microemulsions as reaction medium. The Amano acylase from Aspergillus oryzae showed better catalytic activity for the addition reactions of nitromethane with a series of aromatic aldehydes, and a highest yield of 90% was obtained.
Highlights
The Henry reaction is considered one of the most powerful and atom economical C–C bond-formation reactions and is widely employed in organic chemistry
It's very gratifying to see that some Henry reactions have been performed under mild reaction conditions more recently, e.g., solvent free [11,12,13,14], in aqueous media [9,15,16,17] or using enzymes as catalysts [1,18,19,20]
In 2006, the Griengl group reported the first example of a biocatalytic asymmetric Henry reaction catalyzed by hydroxynitrile lyase [18]
Summary
The Henry (nitroaldol) reaction is considered one of the most powerful and atom economical C–C bond-formation reactions and is widely employed in organic chemistry. It's very gratifying to see that some Henry reactions have been performed under mild reaction conditions more recently, e.g., solvent free [11,12,13,14], in aqueous media [9,15,16,17] or using enzymes as catalysts [1,18,19,20]. As one part of our continuing interest in enzyme promiscuity and green chemistry, we wish to report the first examples of biocatalytic Henry reactions in ionic liquid (IL)-based microemulsions (Scheme 1). 1-butyl-3-methylimidazolium hexafluorophosphate ([Bmim][PF6], a hydrophobic ionic liquid, was selected as oil phase, and the acylase-catalyzed Henry reaction in w/IL microemulsions was explored (Scheme 1). The acylase-catalyzed Henry reaction in water-in-[Bmim][PF6] microemulsions
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