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 I-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 I-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.
Original language | English (US) |
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Article number | 524 |
Journal | Nature communications |
Volume | 2 |
Issue number | 1 |
DOIs | |
State | Published - 2011 |
Externally published | Yes |
ASJC Scopus subject areas
- General Chemistry
- General Biochemistry, Genetics and Molecular Biology
- General
- General Physics and Astronomy
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CCDC 844422: Experimental Crystal Structure Determination
Song, X. (Contributor), Wang, W. (Contributor), Song, A. (Contributor), Zhang, F. (Contributor) & Li, H.-X. (Contributor), Cambridge Crystallographic Data Centre, 2012
DOI: 10.5517/ccxbpfb, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccxbpfb&sid=DataCite
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