1.
Chem Commun (Camb)
; 59(26): 3862-3865, 2023 Mar 28.
Article
in English
| MEDLINE
| ID: mdl-36883973
ABSTRACT
Herein, we report an intramolecular endo-selective Heck reaction of iodomethylsilyl ethers of phenols and alkenols. The reaction leads to the formation of seven- and eight-membered siloxycycles in excellent yields, which could be further converted into the corresponding allylic alcohols upon oxidation. Thus, this method could be used for the selective (Z)-hydroxymethylation of o-hydroxystyrenes and alkenols. Rapid scan EPR experiments and DFT calculations suggest a concerted ß-hydrogen elimination event to take place in the triplet state.