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Synfacts 2011(7): 0765-0765
DOI: 10.1055/s-0030-1260502
DOI: 10.1055/s-0030-1260502
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Pd-Catalyzed Pyridine-Directed Aerobic Olefination of Unactivated sp³ C-H Sites
Contributor(s):Paul Knochel, Andreas K. SteibK. J. Stowers, K. C. Fortner, M. S. Sanford*
University of Michigan, Ann Arbor, USA
Aerobic Pd-Catalyzed sp³ C-H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes
J. Am. Chem. Soc. 2011, 133: 6541-6544
University of Michigan, Ann Arbor, USA
Aerobic Pd-Catalyzed sp³ C-H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes
J. Am. Chem. Soc. 2011, 133: 6541-6544
Further Information
Publication History
Publication Date:
17 June 2011 (online)
Key words
C-H olefination - alkenylation - palladium
Significance
A new palladium/polyoxometalate-catalyzed aerobic olefination of unactivated sp³ C-H bonds has been developed. Nitrogen-containing heterocycles act as directing groups and the products undergo reversible intramolecular Michael addition to form bicyclic nitrogen-containing scaffolds.
Comment
The cationic bicyclic products undergo further synthetic transformations. For example, PtO2-catalyzed hydrogenation yields piperidines, and reduction with NaBH4 gives 1,2,3,6-tetrahydropyridines. The pyridinium products can also be converted into the corresponding alkenes under basic conditions.