One-Pot Domino Catalysis to Construct Alkyl/Aryl Pyrroles Initiated by Pd-TMM Annulation of Unactivated Imines
Herein, a one-pot domino catalyzed three-component process is described, which is initiated by a palladium/zinc cooperatively catalyzed cycloaddition between trimethylenemethane (TMM) and unactivated alkyl/aryl imines, followed by one-pot isomerization and Zn(OTf)<sub>2</sub>-catalyzed DDQ oxidation, furnishing valuable substituted pyrroles. We disclose that the palladium/zinc cooperative catalysis affords a dual-Zn(OTf)<sub>2</sub>-stabilized azapalladacycle, wherein the Pd-N bond is polarized by Zn(OTf)<sub>2</sub>, facilitating a unique outer-sphere allylic amination. Moreover, subsequent DDQ dehydrogenation can be feasibly promoted by zinc catalysis.
Authors
- Xueqin Wei (ORCID: https://orcid.org/0000-0003-2841-3950)
- Xueqiu Huang
- Ying Chen (ORCID: https://orcid.org/0000-0002-7322-2224)
- Xiaofeng Liang (ORCID: https://orcid.org/0000-0001-8248-3816)
- Shuyuan Liang (ORCID: https://orcid.org/0009-0007-6060-9888)
Institutions
- Guangxi University (CN)
- Guangxi Medical University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-01-09
- DOI
- https://doi.org/10.1021/acs.orglett.4c04281
- Citations
- 2
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Natural Science Foundation of Guangxi Zhuang Autonomous Region
- National Natural Science Foundation of China