Rhodium-catalyzed anti-Markovnikov addition of secondary amines to arylacetylenes at room temperature

Kazunori Sakai; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1021/ol201453h

Rhodium-catalyzed anti-Markovnikov addition of secondary amines to arylacetylenes at room temperature

Org Lett. 2011 Aug 5;13(15):3928-31. doi: 10.1021/ol201453h. Epub 2011 Jun 24.

Authors

Kazunori Sakai¹, Takuya Kochi, Fumitoshi Kakiuchi

Affiliation

¹ Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Yokohama, Kanagawa 223-8522, Japan.

PMID: 21699251
DOI: 10.1021/ol201453h

Abstract

An efficient method for synthesis of E-enamines by the anti-Markovnikov addition of secondary amines to terminal alkynes is described. The reaction of a variety of aryl- and heteroarylacetylenes proceeded at room temperature using a combination of a 8-quinolinolato rhodium complex and P(p-MeOC(6)H(4))(3) as a catalyst. The products were obtained as enamines by simple bulb-to-bulb distillation.