Silver-Catalyzed Doyle–Kirmse Reaction of Allyl Sulfides with Vinyl Triftosylhydrazones
Here, we report a general and practical Doyle-Kirmse reaction of allyl/propargyl sulfides with donor-only vinyl carbenes generated <i>in situ</i> from vinyl triftosylhydrazones in the presence of a silver catalyst. This protocol features mild conditions, exhibits a broad substrate scope and exceptional functional group tolerance, and provides corresponding 1,5-dienyl and 1,4-enallenyl sulfides in high yields. Moreover, gram-scale synthesis, late-stage modifications of complex molecules, and post-synthetic transformations were performed to demonstrate the applicability of this protocol.
Authors
- Yong Yang (ORCID: https://orcid.org/0000-0001-8872-2777)
- Xihe Bi (ORCID: https://orcid.org/0000-0002-6694-6742)
- Zhaohong Liu (ORCID: https://orcid.org/0000-0001-9951-8675)
- Paramasivam Sivaguru (ORCID: https://orcid.org/0000-0003-2225-0054)
- Kuan Wang (ORCID: https://orcid.org/0000-0001-8010-9740)
- Ziying Li (ORCID: https://orcid.org/0000-0003-0554-6961)
- Karunanidhi Murali (ORCID: https://orcid.org/0000-0002-6626-627X)
Institutions
- Northeast Normal University (CN)
- Nankai University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-07
- DOI
- https://doi.org/10.1021/acs.orglett.5c01059
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Department of Science and Technology of Jilin Province