Abstract
A new palladium-catalyzed picolinamide (PA)-directed ortho-iodination reaction of ϵ-C(sp2 )-H bonds of γ -arylpropylamine substrates is reported. This reaction proceeds selectively with a variety of γ-arylpropylamines bearing strongly electron-donating or withdrawing substituents, complementing our previously reported PA-directed electrophilic aromatic substitution approach to this transformation. As demonstrated herein, a three step sequence of Pd-catalyzed γ-C(sp3)-H arylation, Pd-catalyzed ϵ -C(sp2 )-H iodination, and Cu-catalyzed C-N cyclization enables a streamlined synthesis of tetrahydroquinolines bearing diverse substitution patterns.
Original language | English (US) |
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Pages (from-to) | 1243-1249 |
Number of pages | 7 |
Journal | Beilstein Journal of Organic Chemistry |
Volume | 12 |
DOIs | |
State | Published - Jun 17 2016 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry