Work

Copper-Catalyzed Petasis-Type Reaction Enables Efficient Synthesis of C1-Substituted Tetrahydro-β-carbolines

Year: 2026

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide Petasis and Petasis-type reactions represent a powerful transformation for constructing a wide array of functionalized amines from simple amines, aldehydes, and organoborons. An α-oxygen or α-nitrogen directing group on the aldehyde component is typically required to facilitate carbon transfer from organoboron to the iminium ion. Herein, we report the first Petasis-type reaction of previously unexplored N -alkyl dihydro-β-carbolinium (DHβC) ions with aryl/alkenyl boronates through novel copper catalysis. The efficiency and utility of this protocol were demonstrated by a broad substrate scope (51 examples, up to 99% yield), excellent scalability (gram scale), and versatile transformations of products. Mechanistic studies suggest that this process proceeds via a novel mechanism involving a copper-mediated intramolecular single-electron transfer (SET). This novel Petasis-type reaction not only significantly broadens the scope of Petasis reactions but also reveals new mechanistic pathways.

Source: Organic Letters

DOI: 10.1021/acs.orglett.6c01466

Authors: Kai Cheng, Jialong Li, Shucai Cai, Jianyi Wang, Lixin Liang, Rongbiao Tong

Institutions: Guangxi University, Hong Kong University of Science and Technology

Language: English

Topic: Synthesis and bioactivity of alkaloids

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Natural Science Foundation of Guangxi Zhuang Autonomous Region, Research Grants Council, University Grants Committee, Natural Science Foundation of Guangxi Province, Guangxi University