Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides

The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP*, lithium arylborates are cross-coupled with tert-butyl -bromopropionate in an enantioconvergent manner, enabling facile access to various op...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 55; no. 8; pp. 1128 - 1131
Main Authors Iwamoto, Takahiro, Okuzono, Chiemi, Adak, Laksmikanta, Jin, Masayoshi, Nakamura, Masaharu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.01.2019
Royal Society of Chemistry
Subjects
Bromides
Catalysis
Chemical industry
Chemistry
Chemistry, Multidisciplinary
Chirality
Cross coupling
Enantiomers
Iron chlorides
Lithium
Nonsteroidal anti-inflammatory drugs
Optical activity
Physical Sciences
Science & Technology
HALIDES
SECONDARY
ALPHA-BROMO ESTERS
METAL
CROSS-COUPLINGS
GRIGNARD-REAGENTS
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Summary:The first iron-catalysed enantioselective Suzuki-Miyaura coupling reaction has been developed. In the presence of catalytic amounts of FeCl2 and (R,R)-QuinoxP*, lithium arylborates are cross-coupled with tert-butyl -bromopropionate in an enantioconvergent manner, enabling facile access to various optically active -arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP* is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc09523j