Palladium(ii)-catalyzed -selective hydroarylation of alkenyl carbonyl compounds with arylboronic acids

A catalytic -selective syn-hydroarylation of alkenyl carbonyl compounds using arylboronic acids has been developed using a substrate directivity approach with a palladium(ii) catalyst. This method tolerates a wide range of functionalized (hetero)arylboronic acids and a variety of substitution patter...

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Published inChemical science (Cambridge) Vol. 9; no. 44; pp. 8363 - 8368
Main Authors Matsuura, Rei, Jankins, Tanner C., Hill, David E., Yang, Kin S., Gallego, Gary M., Yang, Shouliang, He, Mingying, Wang, Fen, Marsters, Rohan P., McAlpine, Indrawan, Engle, Keary M.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.11.2018
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CATALYZED ASYMMETRIC 1,4-ADDITION
1,6-ADDITION
PALLADIUM
ARYL BORONIC ACIDS
REAGENTS
HECK ARYLATIONS
BENZOFURANS
HYDROCARBOFUNCTIONALIZATION
UNACTIVATED ALKENES
CONJUGATE ADDITION
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Summary:A catalytic -selective syn-hydroarylation of alkenyl carbonyl compounds using arylboronic acids has been developed using a substrate directivity approach with a palladium(ii) catalyst. This method tolerates a wide range of functionalized (hetero)arylboronic acids and a variety of substitution patterns on the alkene. Preliminary mechanistic studies suggest that transmetalation is rate-limiting.
ISSN:2041-6520
2041-6539
DOI:10.1039/c8sc03081b