Abstract
A mechanistically divergent method is described that, employing a commercially available hypervalent iodine(III) reagent, generates alkoxy radicals from 1 degrees, 2 degrees, and 3 degrees alcohols and allows their use in the functionalization of C(sp(3))-H and C(sp(2))-H bonds. This visible-light photoredox catalysis produces alkyl ethers via 1,5/6-hydrogen atom transfer or aryl ethers via 1,5-addition. This mild methodology provides a practical strategy for the synthesis of acetals, orthoesters, tetrahydrofurans, and chromanes.
Original language | English |
---|---|
Pages (from-to) | 8436-8440 |
Number of pages | 5 |
Journal | Organic letters |
Volume | 22 |
Issue number | 21 |
DOIs | |
Publication status | Published - 6-Nov-2020 |
Externally published | Yes |
Keywords
- STEREOSELECTIVE-SYNTHESIS
- HYDROGEN-ATOM
- ARYL ETHERS
- FUNCTIONALIZATION
- CYCLIZATION
- OXIDATION
- RING