Rhodium-Catalyzed Synthesis of Sulfur Ylides Via in Situ Generated Iodonium Ylides
Overview
Chemistry
Affiliations
A convenient strategy for the synthesis of sulfur ylides via rhodium-catalyzed coupling of in situ generated iodonium ylides with sulfides or sulfoxides has been developed. A wide range of sulfur ylides were obtained in moderate to good yields from inexpensive sulfur compounds and active methylene compounds with a short reaction time (MW, 5-10 min) or 12-16 h at rt. Furthermore, these sulfoxonium ylides were used as novel acceptor/acceptor carbenes for N-H insertion reactions.
Recent Developments in Stereoselective Reactions of Sulfoxonium Ylides.
OShaughnessy C, Mondal M, Kerrigan N Molecules. 2025; 30(3).
PMID: 39942761 PMC: 11820446. DOI: 10.3390/molecules30030655.
Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents.
Yoshimura A, Zhdankin V Chem Rev. 2024; 124(19):11108-11186.
PMID: 39269928 PMC: 11468727. DOI: 10.1021/acs.chemrev.4c00303.
Visible Light-Promoted Regioselective Benzannulation of Vinyl Sulfoxonium Ylides with Ynoates.
Davas D, Gopalakrishnan D, Kumar S, Anmol , Karmakar T, Vaitla J JACS Au. 2024; 4(3):1073-1080.
PMID: 38559716 PMC: 10976606. DOI: 10.1021/jacsau.3c00802.
Electro-oxidative quinylation of sulfides to sulfur ylides in batch and continuous flow.
Huang X, Yao Y, Yin X, Guan W, Yuan C, Fang Z iScience. 2024; 27(1):108605.
PMID: 38174319 PMC: 10762464. DOI: 10.1016/j.isci.2023.108605.
The thiol-sulfoxonium ylide photo-click reaction for bioconjugation.
Wan C, Hou Z, Yang D, Zhou Z, Xu H, Wang Y Chem Sci. 2023; 14(3):604-612.
PMID: 36741507 PMC: 9847666. DOI: 10.1039/d2sc05650j.