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

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Abstract

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 α-bromopropionate in an enantioconvergent manner, enabling facile access to various optically active α-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.

Graphical abstract: Iron-catalysed enantioselective Suzuki–Miyaura coupling of racemic alkyl bromides

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Publication details

The article was received on 03 Dec 2018, accepted on 27 Dec 2018 and first published on 10 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC09523J
Citation: Chem. Commun., 2019, Advance Article
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    Iron-catalysed enantioselective Suzuki–Miyaura coupling of racemic alkyl bromides

    T. Iwamoto, C. Okuzono, L. Adak, M. Jin and M. Nakamura, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09523J

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