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
- Chemistry(all)
- Biochemistry, Genetics and Molecular Biology(all)
- General
- Physics and Astronomy(all)