Multicomponent Reaction of Isocyanide, Ditelluride, and Mn(III) Carboxylate: Synthesis of N-Acyl Tellurocarbamate

Abstract

A multicomponent reaction of isocyanides, ditellurides and manganese(III) carboxylates under mild reaction conditions leads to the synthesis of various N-acyl tellurocarbamates. This method demonstrates good functional tolerance and broad substrate scope and, as a result, is especially suitable for the postfunctionalization of complicated molecules such as drugs. The given method can be further extended to the synthesis of selenocarbamates.

Electrochemically-driven difunctionalization of the isocyanide and Mumm rearrangement cascade: expeditious synthesis of N-acyl–N-alkyl S-thiocarbamates

“…4 Addressing this limitation, Xu and Tan introduced a multicomponent reaction (MCR) involving isocyanides, ditellurides/diselenides, and manganese( iii ), leading to the synthesis of various N -acyl telluro/selenocarbamates (Scheme 1a). 5 The drawback of this methodology lies in the unsuccessful use of disulfide in the MCR, along with the requirement for excess stoichiometric equivalents of Mn( iii ) aliphatic and aromatic carboxylates as coupling partners. Hence, there remains a pressing need for a simple, direct, and environmentally friendly approach for the formation of C–S bonds to access N -acyl– N -alkyl S -thiocarbamates.…”

Triple-Consecutive Isocyanide Insertions with Aldehydes: Synthesis of 4-Cyanooxazoles

“…Therefore, exploring new selective multiple isocyanide insertion remains to be a challenging and formidable task. During our continual studies based on the isocyanide chemistry, we recently reported a silver-assisted oxidative coupling of ethers and tert -butyl isocyanide to afford β-carbonyl α-iminonitriles involving double-isocyanide insertions (Scheme d), in which a benzoxy cation was proposed as the key intermediate. These results prompted us to produce β-carbonyl α-iminonitriles by replacing ether with readily available aldehyde through direct acyl C–H bond isocyanide insertion of aldehyde.…”