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

Xixi Song, Aiguo Song, Fang Zhang, He-Xing Li () and Wei Wang ()
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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

Nature Communications, 2011, vol. 2, issue 1, 1-10

Abstract: 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.

Date: 2011
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:2:y:2011:i:1:d:10.1038_ncomms1541

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DOI: 10.1038/ncomms1541

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