Journal
ORGANIC LETTERS
Volume 15, Issue 13, Pages 3440-3443Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol4015078
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Funding
- Pennsylvania State University
- US National Science Foundation [CHE-1055795]
- ACS-PFR [51705-DNI1]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1055795] Funding Source: National Science Foundation
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A new strategy for the synthesis of tetrahydroquinolines (THQs) via the sequential functionalizations of remote C-H bonds is reported. This method uses a single picolinamide directing/protecting group to effect Pd-catalyzed gamma-C(sp(3))-H arylation, metal-free epsilon-C(sp(2)) H iodination, and Cu-catalyzed intramolecular C-N cross-coupling. The overall sequence is efficient and versatile, and offers a streamlined synthesis of THQs with complex substitution patterns from readily available aryl iodide and aliphatic amine precursors.
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