Anti-Markovnikov Addition of Anilines to Aliphatic Terminal Alkynes Catalyzed by an 8-Quinolinolato Rhodium Complex

Anti-Markovnikov addition of anilines to aliphatic terminal alkynes proceeded using an 8-quinolinolato rhodium/phosphine catalyst system. The use of a strong organic base, 1,1,3,3,-tetramethylguanidine, in the catalyst system enabled the formation of the aldimine products. Substrates with various functional groups including polar groups such as a phenolic hydroxy group are applicable to the hydroamination.

Automated summary

The anti-Markovnikov addition of anilines to aliphatic terminal alkynes was achieved using an 8-quinolinolato rhodium/phosphine catalyst system, with the formation of aldimine products facilitated by the use of a strong organic base, 1,1,3,3,-tetramethylguanidine. Substrates with various functional groups, including polar groups like phenolic hydroxy group, are suitable for hydroamination.