We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Cross-Coupling of α-Carbonyl Sulfoxonium Ylides with C−H Bonds.
- Authors
Barday, Manuel; Janot, Christopher; Halcovitch, Nathan R.; Muir, James; Aïssa, Christophe
- Abstract
The functionalization of carbon-hydrogen bonds in non-nucleophilic substrates using α-carbonyl sulfoxonium ylides has not been so far investigated, despite the potential safety advantages that such reagents would provide over either diazo compounds or their in situ precursors. Described herein are the cross-coupling reactions of sulfoxonium ylides with C(sp2)−H bonds of arenes and heteroarenes in the presence of a rhodium catalyst. The reaction proceeds by a succession of C−H activation, migratory insertion of the ylide into the carbon-metal bond, and protodemetalation, the last step being turnover-limiting. The method is applied to the synthesis of benz[c]acridines when allied to an iridium-catalyzed dehydrative cyclization.
- Subjects
CARBONYL compounds; HYDROGEN bonding; NUCLEOPHILIC catalysis; RHODIUM; YLIDES
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 42, p13297
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201706804