Potassium (E)-Alkenylaryltrifluoroborates: Orthogonal Functionalization of Haloaryltrifluoroborates via Heck-Mizoroki Reaction

A series of di‐ or trisubstituted alkene‐containing potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium‐catalyzed Heck–Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki–Miyaura cross‐coupling reaction o...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 355; no. 11-12; pp. 2459 - 2465
Main Authors Song, Jung Ho, Kim, Taejung, Lee, Jae Wook, Moon, Soo-Yeon, Kim, Won-Suk, Ham, Jungyeob
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 12.08.2013
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Heck-Mizoroki reaction
microwave irradiation
Physical Sciences
potassium (E)-alkenylaryltrifluoroborates
Science & Technology
Suzuki-Miyaura reaction
PALLADIUM COMPLEXES
ANIONIC-POLYMERIZATION
Heck-Mizoroki reaction
N-HETEROCYCLIC CARBENES
SUZUKI-MIYAURA
CATALYZED HECK
BORONIC ACIDS
CROSS-COUPLING REACTIONS
LIGANDS
microwave irradiation
potassium (E)-alkenylaryltrifluoroborates
EFFICIENT
ARYL CHLORIDES
Suzuki-Miyaura reaction
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Summary:A series of di‐ or trisubstituted alkene‐containing potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium‐catalyzed Heck–Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki–Miyaura cross‐coupling reaction of these alkenylaryltrifluoroborates was successfully carried out with aryl and alkenyl bromides using 5 mol% of tetrakis(triphenylphosphine)palladium(0) and 3.0 equiv. of cesium carbonate in aqueous 1,4‐dioxane under microwave irradiation.
Bibliography:KIST institutional program - Project No. 2Z03840
Basic Science Research Program through the National Research Foundation of Korea (NRF)
ark:/67375/WNG-GWBC2WG1-S
istex:3B4D9EB18B8AAE4905ADB53DE523B57830DE650F
ArticleID:ADSC201300294
Ministry of Education, Science and Technology - No. NRF-2012R1A1A1006123
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201300294