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Title: Metal-free access to (spirocyclic) tetrahydro-β-carbolines in water using an ion-pair as a superacidic precatalyst
Authors: Zhang, Zhenguo
Liu, Xiaoxiao
Ji, Liang
Zhang, Ting
Jia, Zhenhua
Loh, Teck-Peng
Keywords: Science::Chemistry
Issue Date: 2022
Source: Zhang, Z., Liu, X., Ji, L., Zhang, T., Jia, Z. & Loh, T. (2022). Metal-free access to (spirocyclic) tetrahydro-β-carbolines in water using an ion-pair as a superacidic precatalyst. ACS Catalysis, 12(3), 2052-2057.
Journal: ACS Catalysis 
Abstract: The unprecedented triarylcarbonium ion-pair-catalyzed Pictet-Spengler reaction of tryptamines with aromatic aldehydes and cyclic ketones in water was disclosed. Under metal-free conditions, diverse tetrahydro-β-carbolines and spirocyclic tetrahydro-β-carbolines were obtained in good yields with excellent functional group tolerance, including late-stage modification of natural products and small molecular drugs. The practicability of this protocol is also characterized in the gram-scale synthesis of Komavine and several other functional compounds. Preliminary mechanistic studies indicated that in aqueous media the in situ-generated superacidic species from the carbonium ion pair with water was crucial to promote the Pictet-Spengler reaction.
ISSN: 2155-5435
DOI: 10.1021/acscatal.1c05546
Schools: School of Physical and Mathematical Sciences 
Rights: © 2022 American Chemical Society. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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