10.1021/jo400246d.s004
Sandeep
N. Raikar
Sandeep
N.
Raikar
Helena C. Malinakova
Helena C.
Malinakova
Divergent Reaction Pathways of Homologous and Isosteric
Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the
Synthesis of Heterocycles
American Chemical Society
2016
Ru
Divergent Reaction Pathways
terminal arylalkynes
sequential addition
RCM
Heck cyclization
enyne
isosteric groups
Isosteric Propargyl Amides
ring size
benzoyl chloride
CH vs N
heterocyclic dienes
Pd catalysts
cyclization pathways
2016-02-19 11:21:51
Dataset
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/2422387
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 (<i>n</i> =
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.