The Triple Role of Fluoride Ions in Palladium-Catalyzed Suzuki-Miyaura Reactions: Unprecedented Transmetalation from [ArPdFL2] Complexes

Fluoride ions play three roles in the Suzuki–Miyaura reaction. They favor the reaction by formation of trans‐[ArPdF(PPh3)2], which reacts with Ar′B(OH)2 in an unprecedented rate‐determining transmetalation, and by promoting the reductive elimination from the trans‐[ArPdAr′(PPh3)2] intermediate. Conv...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 51; no. 6; pp. 1379 - 1382
Main Authors Amatore, Christian, Jutand, Anny, Le Duc, Gaëtan
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 06.02.2012
WILEY‐VCH Verlag
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
aryl boronic acid
fluoride ions
Fluorides
Formations
Palladium
reaction mechanism
Suzuki-Miyaura reactions
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Summary:Fluoride ions play three roles in the Suzuki–Miyaura reaction. They favor the reaction by formation of trans‐[ArPdF(PPh3)2], which reacts with Ar′B(OH)2 in an unprecedented rate‐determining transmetalation, and by promoting the reductive elimination from the trans‐[ArPdAr′(PPh3)2] intermediate. Conversely, F− disfavors the reaction by formation of unreactive anionic Ar′B(OH)n−3Fn− (n=1–3), leading to two antagonistic effects of F− in the transmetalation.
Bibliography:ark:/67375/WNG-DD074JJV-0
CNRS
UPMC
CNRS, ENS, and UPMC are thanked for financial support.
ENS
istex:46F1C4ACC1C3E414F4B43FD1558AFFDC7DE4DA03
ArticleID:ANIE201107202
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201107202