An Efficient and Eco‐Friendly Synthesis of Protoberberine and 13‐Me Protoberberine Alkaloids via Electrochemical Acceptorless Dehydrogenation
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Published:2023-02-27
Issue:7
Volume:15
Page:
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ISSN:1867-3880
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Container-title:ChemCatChem
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language:en
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Short-container-title:ChemCatChem
Author:
Li Weijian1,
Huang Shiqi2,
Jiang Meifen3,
Chen Yu1,
Yang Zhi1,
Tang Pei1ORCID,
Chen Fener123ORCID
Affiliation:
1. Sichuan Research Center for Drug Precision Industrial Technology West China School of Pharmacy Sichuan University Chengdu 610041 China
2. Institute of Pharmaceutical Sciences Zhengzhou University Zhengzhou 450001 China
3. Engineering Center of Catalysis and Synthesis for Chiral Molecules Department of Chemistry Fudan University Shanghai 200433 China
Abstract
AbstractA practicable and environmentally benign process for the synthesis of protoberberine (PB) and 13‐methylprotoberberine (13‐MePB) alkaloids is reported. In contrast to previous dehydrogenation of saturated C ring utilizing a stoichiometric oxidant, the electrocatalytic approach through I2‐mediated electrochemical acceptorless dehydrogenation (ECAD) can eco‐efficiently construct aromatized C ring of PBs and 13‐MePBs in last‐stage. This new method to the aromatization of tetracyclic framework has been applied to divergent syntheses of ten PBs and eight 13‐MePBs in high yields. Importantly, this I2‐ECAD protocol can be conducted on a gram scale and applied in a continuous‐flow microreactor successfully. Given such practicability and efficiency, the developed synthetic strategy meets many salient features of green chemistry, and would be greatly beneficial to the synthesis of important isoquinoline fine chemicals and relevant natural products.
Funder
National Natural Science Foundation of China
Subject
Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis