Palladium(O) and Phase Transfer Catalyzed Conversion of Azirines to Styrylindoles

Abstract

o l e s were obtained i n modest y i e l d s by t h e exposure of a z i r i n e s t o carbon monoxide, a palladium(0) c a t a l y s t , sodium hydroxide, benzene as the organic phase, and b e n z y l t r i e t h y lamnonium c h l o r i d e as the phase t r a n s f e r agent.The r e a c t i o n i s sens i t i v e t o t h e arrnosphere used. The chemistry o f a z i r i n e s has been extensively investigated i n recentThe metal complex catalyzed r i n g opening o f a z i r i n e s has l e d t o the development of several useful r e a c t i o n processes!Of p a r t i c u l a r n o t e a r e palladium(0) catalyzed reactions, the course of which depends on the nature of the metal c a t a l y s t .When a z i r i n e s ( 1 ) a r e exposed t o carbon monoxide i n t h e presence o f a c a t a l y t i c amount o f tetrakis[triphenylphosphine)palladium(0), b i c y c l i c 8-lactams (2) a r e However, v i n y l isocyanates (3) are obtained i n a regiospecific manner using bis(dibenzy1idene-