Dimethoxyacetaldehyde-<i>N</i>-triftosylhydrazone: Preparation and Carbene Reactivity in Cyclopropanation and Doyle–Kirmse Reactions
Herein, we developed the new, powerful, and easy-to-handle chemical reagent, dimethoxyacetaldehyde-<i>N</i>-triftosylhydrazone (DMHz-Tfs), as a convenient in situ source of dimethoxydiazoethane under mild conditions. We demonstrate the carbene reactivity of DMHz-Tfs in iron-catalyzed cyclopropanation and Doyle-Kirmse reactions, providing access to diverse acetal functionalized cyclopropanes and homoallylic- and allenyl-sulfides at gram-scale with high stereoselectivity. DFT calculations elucidated the involvement of the most stable doublet spin state iron-carbene intermediate over other possible spin states.
Authors
- Hongzhu Chen (ORCID: https://orcid.org/0000-0001-5338-0041)
- Yongquan Ning (ORCID: https://orcid.org/0000-0001-8791-6254)
- Zeyun Liu (ORCID: https://orcid.org/0000-0003-4547-2135)
- Yong Wu (ORCID: https://orcid.org/0000-0002-6806-1817)
- Paramasivam Sivaguru (ORCID: https://orcid.org/0000-0003-2225-0054)
- Yifan Zhang (ORCID: https://orcid.org/0000-0002-5908-9164)
- Xiaolong Zhang (ORCID: https://orcid.org/0000-0002-9423-1461)
- Shuang Li (ORCID: https://orcid.org/0000-0002-3483-5087)
- Karunanidhi Murali (ORCID: https://orcid.org/0000-0002-6626-627X)
- Wei Song (ORCID: https://orcid.org/0009-0000-5612-7228)
Institutions
- Beihua University (CN)
- Northeast Normal University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c00223
- Citations
- 3
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Education Department of Jilin Province
- Department of Science and Technology of Jilin Province