Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines Using Reductive Methylation Step

Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines based on reductive methylation of ortho-iodoanilines using CH2O–NaBH3CN and coupling with terminal diacetylens was developed. Altered sequence including dimethylation of 2-(buta-1,3-diynyl)anilines was also successfully achieved and gave higher overall yields in the case of anilines without acceptor substituent in the ring.