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A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water.

ABSTRACT: Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4'-arylated phenylalanines and tyrosines in good yields at low catalyst loading with a wide functional group tolerance.

SUBMITTER: Peramo A

PROVIDER: S-EPMC7146153 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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A Self-Assembling NHC-Pd-Loaded Calixarene as a Potent Catalyst for the Suzuki-Miyaura Cross-Coupling Reaction in Water.

Peramo Arnaud A Abdellah Ibrahim I Pecnard Shannon S Mougin Julie J Martini Cyril C Couvreur Patrick P Huc Vincent V Desmaële Didier D

Molecules (Basel, Switzerland) 20200324 6

Nanoformulated calix[8]arenes functionalized with <i>N</i>-heterocyclic carbene (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol arylborates at low temperature in water without any organic co-solvent. Combined with an improved one-step synthesis of triol arylborates from boronic acid, this remarkably efficient new tool provided a variety of 4'-arylated phenylalanines and ...[more]

PMID: 32213875

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