Rh-Catalyzed C–H Alkynylation of Indole Derivatives with Silver(I)-Controlled Regiodivergence
We have disclosed silver(I)-induced switching of regioselectivity in rhodium-catalyzed C-H alkynylation of indole derivatives with the help of a pivaloyl directing group by tuning C-H metalation modes. The judicious choice of AgOAc, Ag<sub>2</sub>O, and Ag<sub>2</sub>CO<sub>3</sub> affords an array of C2-alkynylated indoles, C4-alkynylated indoles, and C2,C4-dialkynylated indoles, respectively. The synthetic utility of the alkyne fragment is demonstrated by derivatization into valuable indole-based compounds.
Authors
- Shuangliang Zhao (ORCID: https://orcid.org/0000-0002-9547-4860)
- Taoyuan Liang (ORCID: https://orcid.org/0000-0002-7509-5927)
- Yaokun Zhao
- Zhuan Zhang (ORCID: https://orcid.org/0000-0003-4841-4109)
- Xing Han (ORCID: https://orcid.org/0000-0002-7921-8197)
- Pengfei Zhou
- Chenjie Zhang
- Xingchi Li
Institutions
- Guangxi University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-08-23
- DOI
- https://doi.org/10.1021/acs.orglett.4c02151
- Citations
- 8
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.00
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology, Guangxi University