Ligand-enabled palladium-catalyzed hydroesterification of vinyl arenes with high linear selectivity to access 3-arylpropanoate esters

Palladium-catalyzed linear-selective hydroesterification of vinyl arenes with alcohols enabled by diphosphine ligands derived from bis[2-(diphenylphosphino)ethyl]amides has been developed. A variety of 3-arylpropanoate esters were obtained in high yields and regioselectivity. The robustness of this...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 24; pp. 3921 - 3924
Main Authors Deng, Zhixin, Han, Sheng, Ke, Miaolin, Ning, Yingtang, Chen, Fen-Er
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 22.03.2022
Royal Society of Chemistry
Subjects
Alcohols
Amides
Aromatic compounds
Catalysis
Chemistry
Chemistry, Multidisciplinary
Esters
Ligands
Palladium
Physical Sciences
Regioselectivity
Science & Technology
Selectivity
ALKENES
ALKOXYCARBONYLATION
CARBONYLATION REACTIONS
CARBON-MONOXIDE
METHYL PROPANOATE
COMPLEXES
STYRENE
ALKYNES
ETHENE
METHOXYCARBONYLATION
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Summary:Palladium-catalyzed linear-selective hydroesterification of vinyl arenes with alcohols enabled by diphosphine ligands derived from bis[2-(diphenylphosphino)ethyl]amides has been developed. A variety of 3-arylpropanoate esters were obtained in high yields and regioselectivity. The robustness of this methodology was further demonstrated by the efficient gram-scale synthesis of the ethyl 3-phenylpropanoate as a precursor to hydrocinnamic acid. A series of diphosphine ligands derived from bis[2-(diphenylphosphino)ethyl]amide have proved to be powerful for the linear selective Pd-catalyzed hydroesterification of vinyl arenes.
Bibliography:10.1039/d2cc00228k
Electronic supplementary information (ESI) available. See DOI
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc00228k