Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 42, Pages 10766-10772Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801031
Keywords
benzofulvenes; C-H insertion; chemoselectivity; dual gold catalysis; gold vinylidenes
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Funding
- Brazilian Council for Scientific and Technological Development (CNPq, Science without Borders Program)
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An unprecedented, often almost quantitative access to tricyclic aromatic compounds by dual gold catalysis was developed. This synthetic route expands the scope of benzofulvene derivatives through a C(sp(2))-H bond insertion in easily available starting materials. The insertion takes place with an exclusive chemoselectivity with respect to the competing aromatic C-H positions. A bidirectional synthesis with two competing ortho-aryl C-H bonds in the selectivity-determining step also shows perfect selectivity; this result is explained by a computational investigation of the two conceivable intermediates. The intramolecular competition of two non-equivalent aryl C-H bonds with a benzylic methyl group also showed perfect selectivity.
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