Pd-Catalyzed Allylic Substitution of Azo-Ene Adducts Enables Net Allylic C–H Alkylation of Allylic Alcohols
We present a protocol for a regioselective allylic C-H alkylation of allylic alcohols, consisting of a sequential azo-ene reaction and attendant Pd-catalyzed allylic substitution with Grignard reagents. Notable features of this work include: (1) regioselective C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation is achieved under Pd-catalysis, and (2) the allylic substitution proceeds with retention of configuration at the electrophilic allylic carbon as well as the olefin geometry.
Authors
- Kiyosei Takasu (ORCID: https://orcid.org/0000-0002-1798-7919)
- Takashi Chiba (ORCID: https://orcid.org/0000-0001-6431-3645)
- Yusuke Kuroda (ORCID: https://orcid.org/0000-0003-0952-7098)
- Moe Kawajiri
Institutions
- Kyoto University (JP)
- Research Foundation ITSUU Laboratory (JP)
- Kumamoto University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-02-03
- DOI
- https://doi.org/10.1021/acs.orglett.5c00049
- Citations
- 3
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- Japan Agency for Medical Research and Development
- Ministry of Education, Culture, Sports, Science and Technology
- Japan Society for the Promotion of Science