AI Article Synopsis
- Researchers have developed a gentle, transition-metal-free method for esterifying thioamides by creating tetrahedral intermediates.
- This marks the first time a transition-metal-free process has successfully converted thioamides to thionoesters in organic chemistry.
- The technique utilizes -Boc-thioamides to destabilize n → π* conjugation, presenting new possibilities for amide bond functionalization.
Article Abstract
Herein, we report an exceedingly mild method for the direct, transition-metal-free esterification of thioamides through the selective generation of tetrahedral intermediates. The method represents the first transition-metal-free approach to the thioamide to thionoester transformation in organic synthesis. This reactivity has been accomplished through -Boc-thioamides that engage in ground-state destabilization of the n → π* conjugation. The ground-state destabilization of "single-atom" bioisosteric thioamides will expand the arsenal of valuable amide bond functionalization reactions.
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| http://dx.doi.org/10.1021/acs.orglett.3c02238 | DOI Listing |
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