New route to ABCD-porphyrins

ORGN 769

Dilek Kiper Dogutan, ddoguta@unity.ncsu.edu and Jonathan S. Lindsey, jlindsey@ncsu.edu. Department of Chemistry, North Carolina State University, Dabney Hall Box 8204, Yarborough Drive, Raleigh, NC 27695-8204
Abstract A new route for preparing porphyrins that bear up to four different meso-substituents (ABCD-porphyrins) has been developed. The route relies on the preparation of a 1-acyl-19-X bilane (1), which is derived from two dipyrromethane species. A lengthy study of suitable X groups, methods for stepwise conversion of 1 to the ABCD-porphyrin 2, and conditions for the latter transformation have been examined. A one-flask transformation also has been identified that gives the ABCD-porphyrin 2 from 1 in 65% yield.