Synfacts 2007(12): 1245-1245  
DOI: 10.1055/s-2007-991401
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

C-H-Activated ortho-Arylation of Anilides and Their Cyclization to Phenanthridines

Contributor(s): Victor Snieckus, Toni Rantanen
D. Shabashov, O. Daugulis*
University of Houston, USA
Further Information

Publication History

Publication Date:
22 November 2007 (online)


An efficient synthesis of 2-aryl- and 2,6-diarylanilides is reported utilizing a palladium-catalyzed direct arylation of N-acyl anilines with various aryl iodides. A steric component is evident in this interesting reaction since ortho-substituted aryl iodides failed. Deacylation using NaOH (3 examples, 85-99% yields) led to the corresponding anilines while trifluoroacetic anhydride afforded phenanthridines. The reaction was run also in one pot, without the need to isolate the intermediate coupling products. In general, the substrate scope was well studied.