Enamides and enesulfonamides as nucleophiles: formation of complex ring systems through a platinum(II)-catalyzed addition/Friedel-Crafts pathway.
Cyclic enamine derivatives (enesulfonamides and enamides) tethered to an 1-arylalkynyl fragment undergo a platinum(II)-catalyzed tandem alkyne addition/Friedel-Crafts ring closure to form nitrogen-containing polycyclic structures. Regioselectivity in the initial addition of the enesulfonamide or enamide nucleophile to the platinum(II)-alkyne complex is important. Electron-rich arenes and heterocycles led to the formation of products resulting from an initial 6-endo cyclization. Twenty-three examples of this process are presented.
Kozak
Jennifer A
JA
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.
Dodd
Jennifer M
JM
Harrison
Tyler J
TJ
Jardine
Katherine J
KJ
Patrick
Brian O
BO
Dake
Gregory R
GR