Synthesis of Unsymmetric Triarylmethanes Bearing CF3-Substituted All-Carbon Quaternary Stereocenters: 1,6-Arylation of δ-Trifluoromethyl Substituted para-Quinone Methides-Reference-Cited by-同舟云学术

Synthesis of Unsymmetric Triarylmethanes Bearing CF3-Substituted All-Carbon Quaternary Stereocenters: 1,6-Arylation of δ-Trifluoromethyl Substituted para-Quinone Methides

Published:2020-08-05 Issue:16 Volume:31 Page:1619-1622
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Ma Shutao¹,Liu Xigong²,Liu Lei¹²^ORCID,Ma Yingang¹,Pang Jingxiang³,Pan Xiaoguang¹

Affiliation:

1. Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University

2. School of Chemistry and Chemical Engineering, Shandong University

3. Shandong Medicinal Biotechnology Center, Key Laboratory for Rare & Uncommon Diseases of Shandong Province, Key Lab for Biotech-Drugs of National Health Commission, Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences

Abstract

Pre-synthesized δ-CF3-δ-aryl-disubstituted para-quinone methides bearing δ-substituents were identified as isolable and storable substrates for 1,6-arylation reactions. A broad range of electron-rich arenes and heteroarenes participated in the arylation process, furnishing a wide array of unsymmetrical CF3-substituted triarylmethanes in high efficiency. The mild and expeditious protocol exhibited broad scopes of both arene and para-quinone methide components.

Funder

National Natural Science Foundation of China

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1706408.pdf

Reference1 articles.

1. Ga(OTf)3-Catalyzed Temperature-Controlled Regioselective Friedel–Crafts Alkylation of Trifluoromethylated 3-Indolylmethanols with 2-Substituted Indoles: Divergent Synthesis of Trifluoromethylated Unsymmetrical 3,3′-and 3,6′-Bis(indolyl)methanes

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3. Remote Functionalization of 8‐Substituted Quinolines with para ‐Quinone Methides: Access to Unsymmetrical Tri(hetero)arylmethanes;European Journal of Organic Chemistry;2022-05-02

4. 1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives;Chinese Journal of Organic Chemistry;2022

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