Pd-Catalyzed Migratory 1,1-Cycloannulation Reaction of Alkenes
Here, we report a novel strategy for the preparation of diverse heterocycles via a Pd-catalyzed migratory 1,1-cycloannulation reaction (MCAR) of alkenes. Starting from readily available alkenyl amines and alkenyl alcohols, this approach allows the formation of a wide range of five- to seven-membered azaheterocycles and oxaheterocycles with high efficiency and good functional group tolerance. The key to the realization of this reaction is the use of 4-iodophenol or 2-iodophenol derivatives where the phenolic hydroxyl group plays a critical role in controlling the direction of migration and the ring-size of the heterocycles through the formation of a quinone methide intermediate.
Authors
- Tao Liu (ORCID: https://orcid.org/0000-0003-2353-1819)
- Yichen Wu (ORCID: https://orcid.org/0000-0002-0639-0412)
- Peng Wang (ORCID: https://orcid.org/0000-0002-6442-3008)
- Jinping Wang
Institutions
- Hangzhou Normal University (CN)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-12-18
- DOI
- https://doi.org/10.1021/jacs.4c14153
- Citations
- 7
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- National Natural Science Foundation of China
- Chinese Academy of Sciences
- Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences
- National Key Research and Development Program of China
- Program of Shanghai Academic Research Leader