TY - DATA T1 - Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles PY - 2016/02/19 AU - Sandeep N. Raikar AU - Helena C. Malinakova UR - https://acs.figshare.com/articles/dataset/Divergent_Reaction_Pathways_of_Homologous_and_Isosteric_Propargyl_Amides_in_Sequential_Ru_Pd_Catalyzed_Annulations_for_the_Synthesis_of_Heterocycles/2422420 DO - 10.1021/jo400246d.s002 L4 - https://ndownloader.figshare.com/files/4064188 KW - Ru KW - Divergent Reaction Pathways KW - terminal arylalkynes KW - sequential addition KW - RCM KW - Heck cyclization KW - enyne KW - isosteric groups KW - Isosteric Propargyl Amides KW - ring size KW - benzoyl chloride KW - CH vs N KW - heterocyclic dienes KW - Pd catalysts KW - cyclization pathways N2 - Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one-pot protocol for the enyne–RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency. ER -