A Novel Electrophilic Diamination Reaction of Alkenes

Guigen Li; Han-Xun Wei; Sun Hee Kim; Michael D Carducci

doi:10.1002/1521-3773(20011119)40:22<4277::AID-ANIE4277>3.0.CO;2-I

A Novel Electrophilic Diamination Reaction of Alkenes

Angew Chem Int Ed Engl. 2001 Nov 19;40(22):4277-4280. doi: 10.1002/1521-3773(20011119)40:22<4277::AID-ANIE4277>3.0.CO;2-I.

Authors

Guigen Li¹, Han-Xun Wei¹, Sun Hee Kim¹, Michael D Carducci²

Affiliations

¹ Department of Chemistry and Biochemistry Texas Tech University, Lubbock, TX 79409-1061, USA, Fax: (+1) 806) 742-1289.
² Department of Chemistry University of Arizona, Tucson, AZ 85721, USA.

PMID: 29712117
DOI: 10.1002/1521-3773(20011119)40:22<4277::AID-ANIE4277>3.0.CO;2-I

Abstract

A three-component electrophilic reaction transforms olefins into imidazoline and diamine derivatives. Rhodium(II) heptafluorobutyrate dimer (2 mol %) was utilized as the catalyst and N,N-dichloro-p-toluenesulfonamide (TsNCl₂ ) and acetonitrile as the nitrogen sources. Modest to good yields (45-82 %) and high regio- and stereoselectivity were achieved.

Keywords: amination; electrophilic additions; homogeneous catalysis; nitrogen heterocycles; rhodium.