Pd-Catalyzed One-Pot Synthesis of Indole-3-carboxylic Acids via a Sequential Water-Mediated Nucleophilic Addition to Amides/Esters and Carbon–Heteroatom Cross-Coupling Reaction Strategy
Using 4-bromoindole-3-carboxylic acid derivatives (amides or esters) as substrates, this paper successfully developed a trace water-promoted, palladium-catalyzed "one-pot" reaction strategy for synthesizing 4-amino/alkoxyindole-3-carboxylic acid products. With PdCl<sub>2</sub> (5 mol %) as the precatalyst, Xantphos as the ligand, and cesium pivalate as the additive, this synthetic method innovatively integrates nucleophilic substitution of amides/esters with Pd-catalyzed C-N or C-O cross-coupling into a single reaction system, achieving efficient synergy of multistep transformations. This approach facilitates a modular and rapid assembly of multisubstituted indole-3-carboxylic acids, exhibiting broad functional group compatibility while maintaining good reaction yields.
Authors
- Gongyuan Zhao (ORCID: https://orcid.org/0000-0002-4406-5426)
- Zhonghui Sun (ORCID: https://orcid.org/0000-0002-3042-7756)
- Kai Hong (ORCID: https://orcid.org/0000-0001-7341-4931)
- Lian‐Xu Shi (ORCID: https://orcid.org/0000-0003-3390-3997)
- T. ZHANG
- Ye Wu
- Chunxia Chen
- Jinsong Peng (ORCID: https://orcid.org/0000-0002-9330-1560)
Institutions
- Culture Resource (EG)
- Innovative Research (United States) (US)
- Northeast Forestry University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-08-28
- DOI
- https://doi.org/10.1021/acs.joc.5c01082
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Heilongjiang Province
- National Key Research and Development Program of China
- Fundamental Research Funds for the Central Universities