Direct Synthesis of Bis(alkylamino)maleonitriles from Alcohols and TMSCN with Bi(OTf)3

Abstract

A direct method for preparing bis(alkylamino)maleonitriles from alcohols was developed. Treatment of tertiary alcohols with trimethylsilyl cyanide (TMSCN) and trimethylsilyl triflate (TMSOTf) in the presence of bismuth(III) triflate [Bi(OTf) 3 ] afforded the corresponding bis(alkylamino)maleonitriles in moderate-to-high yields. Tertiary alcohols with various functional groups such as halo, ether, ester, and imide functional groups were tolerated under these conditions. This is the first report of a synthetic method for the preparation of bis(alkylamino)maleonitriles in a single step from tertiary alcohols.