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Title

CATALYTIC CYANOSILYLATION OF CARBONYL COMPOUNDS BY 4-NITRO POTASSIUM PHTHALIMIDE UNDER MILD CONDITIONS

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Abstract

 CYANOHYDRINS ARE VERSATILE INTERMEDIATES, WHICH CAN EASILY BE CONVERTED INTO WIDE VARIETY OF VALUABLE CLASSES OF COMPOUNDS. CYANOHYDRINS ARE TYPICALLY PREPARED BY THE INTERACTION OF VARIOUS CARBONYL COMPOUNDS WITH A CYANIDE SOURCE SUCH AS TRIMETHYLSILYL CYANIDE (TMSCN) AS NUCLEOPHILE [1]. GENERALLY, IN THE ABSENCE OF A CATALYST, NO REACTION OCCURS BETWEEN TMSCN AND CARBONYL COMPOUNDS. THE CYANOSILYLATION IS PARTICULARLY SUITABLE SINCE THE SILYL PROTECTING GROUPS CAN BE REMOVED UNDER VERY MILD REACTION CONDITIONS [2].IN THIS REPORT 4-NITRO POTASSIUM PHTHALIMIDE (1) WAS SYNTHESIZED AND USED AS A NOVEL AND AN EFFICIENT ORGAN OCATALYST FOR CYANOSILYLATION OF CARBONYL COMPOUNDS UNDER MILD AND SOLVENT-FREE CONDITIONS AFFORDING VARIOUS CYANOHYDRIN TRIMETHYLSILYL ETHERS (SCHEME 1).SINCE THIS REACTION COULD BE PERFORMED WELL IN SOLVENT-FREE CONDITIONS AND HAS NO EFFECTS OF TOXIC SOLVENTS AND WASTES WITH ADDED ADVANTAGES OF RECYCLABILITY FOR THREE TIMES WITHOUT LOSS OF EFFICIENCY, THEREFORE HAS A GOOD POTENTIALITY FOR RECYCLING, IT HELP VALUABLE MATERIALS TO SUSTAIN. AS A RESULT, WASTES LOSS WILL BE DECREASED DRAMATICALLY MAKING THEM IN GOOD AGREEMENT WITH GREEN CHEMISTRY.

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