<i>anti</i>-Hydroarylation of Activated
Internal Alkynes: Merging Pd and Energy Transfer Catalysis
Javier Corpas
Pablo Mauleón
Ramón Gómez Arrayás
Juan C. Carretero
10.1021/acs.orglett.0c02281.s001
https://acs.figshare.com/articles/journal_contribution/_i_anti_i_-Hydroarylation_of_Activated_Internal_Alkynes_Merging_Pd_and_Energy_Transfer_Catalysis/12749757
A general catalytic <i>anti</i>-hydroarylation of electron-deficient
internal alkynes compatible with both electron-poor and electron-rich
aryl reagents is reported. This selectivity is achieved through a
sequential <i>syn</i>-carbopalladation of the alkyne by
an Ar–Pd species, followed by a tandem, Ir-photocatalyzed,
counter-thermodynamic <i>E</i> → <i>Z</i> isomerization. The use of <i>ortho</i>-substituted boronic
acids enables direct access to pharmaceutically relevant heterocyclic
cores via a cascade process. Mechanistic insight into the involvement
of Ar–Pd versus Pd–H as an active species is provided.
2020-07-31 22:15:00
Hydroarylation
sequential syn
ortho
selectivity
heterocyclic cores
Mechanistic insight
species
hydroarylation
electron-rich aryl reagents
access
electron-poor
Merging Pd
counter-thermodynamic
cascade process
Activated Internal Alkynes
pharmaceutically
tandem
involvement
boronic acids
Ir-photocatalyzed
Energy Transfer Catalysis
alkyne
carbopalladation
electron-deficient
Ar
isomerization