1,2-N-Migration of Metal Carbenes In Situ-Derived from Copper-Catalyzed Cyclization of Vinylallenes: Rapid Access to Pyridazine Derivatives
1,2-N-Migration into metal carbenes has proven to be a powerful method for the efficient construction of various valuable N-heterocycles. However, most of them are so far limited to diazo substrates and noble-metal catalysts. Herein, we report a highly selective 1,2-N migration into copper carbenes generated by the copper-catalyzed cyclization of vinylallenes, enabling the practical and atom-economical construction of diverse tetrahydropyridazines. Moreover, employing <sup><i>n</i></sup>Bu-substituted vinylallenes as starting materials, 4-butylidene-tetrahydropyridazines can be exclusively formed in an orderly manner by 1,2-N migration and 1,5-H migration.
Authors
- Dongcan Lv (ORCID: https://orcid.org/0000-0002-7316-663X)
- Kua‐Fei Wei
- Guang-Ce Jiang
- Wen‐Bo Shen (ORCID: https://orcid.org/0000-0003-0416-3571)
- Xiaoming Ji (ORCID: https://orcid.org/0000-0001-6848-2964)
- Qi Guo (ORCID: https://orcid.org/0000-0003-1021-4072)
- Hongtao Wang (ORCID: https://orcid.org/0009-0005-9539-865X)
- Mingqin Zhao
Institutions
- Jingdezhen University (CN)
- Henan Agricultural University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-03-11
- DOI
- https://doi.org/10.1021/acs.joc.6c00283
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00