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Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction

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  • Xixi Song

    (University of New Mexico)

  • Aiguo Song

    (University of New Mexico)

  • Fang Zhang

    (Shanghai Normal University)

  • He-Xing Li

    (Shanghai Normal University)

  • Wei Wang

    (University of New Mexico
    School of Pharmacy, East China University of Science & Technology)

Abstract

Cross-coupling reactions typically rely on the use of transition metal catalysis. However, although achieving this process using metal-free organocatalysts is highly challenging, it could offer unique opportunities to discover novel bond-forming strategies in organic synthesis. Here we report a new amine catalysed direct stereoselective C-H α-arylation reaction of unmodified enals with bromoarenes. The power of this process, which involves an unprecedented iminium-Michael-alkylation-enamine-retro-Michael cascade sequence, has been demonstrated in the context of direct α-functionalization reactions of simple, unmodified enals with 4-bromophenols, 1-bromo-2-naphthol and 3-bromoindoles under mild reaction conditions. Notably, the process can be used for highly stereoselective syntheses of non-readily accessible E isomers, which normally require the use of transition metal-promoted cross-couplings and functionalized enals. The results of these studies significantly expand the scope of aminocatalysis.

Suggested Citation

  • Xixi Song & Aiguo Song & Fang Zhang & He-Xing Li & Wei Wang, 2011. "Direct stereoselective α-arylation of unmodified enals using an organocatalytic cross-coupling-like reaction," Nature Communications, Nature, vol. 2(1), pages 1-10, September.
    • Handle: RePEc:nat:natcom:v:2:y:2011:i:1:d:10.1038_ncomms1541
    DOI: 10.1038/ncomms1541
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