Organo‐Catalyzed Intermolecular Dehydrative Coupling Reaction to Prepare Arylacetic Acid Derivatives

• Published in: Advanced synthesis & catalysis Vol. 366; no. 3; pp. 502 - 507
• Main Authors: Chen, Fei, Geng, Huidan, Zhao, Yonglong, Li, Chun, Guo, Bing, Tang, Lei, Yang, Yuanyong
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 19.02.2024; Wiley Subscription Services, Inc
• Subjects: Amines; atom economic; Chemical reactions; Chemistry; Chemistry, Applied; Chemistry, Organic; Coupling; Dehydration; dehydrative coupling; organo-catalyzed; para-quinone methides; Phenols; Physical Sciences; regioselective; Regioselectivity; Science & Technology; Substrates; PARA-QUINONE METHIDE; DESIGN; atom economic; dehydrative coupling; ALGA RHODOMELA-CONFERVOIDES; regioselective; FUNCTIONALIZATION; para-quinone methides; PHENOLS; organo-catalyzed; CARBOXYLATION; EFFICIENT; HYDROARYLATION; BROMOPHENOLS; ASYMMETRIC REACTIONS
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.202301163

Herein, the use of triphenylmethylium tetrakis(pentafluorophenyl)borate as an efficient catalyst for the intermolecular dehydrative coupling of p‐hydroxymandelic acid hydrate with substituted aromatic amines and (thio)phenols was developed, which allows for the preparation of arylacetic acid derivatives in a convenient manner. Notably, this method offers several advantages, including being prefunctionalization free, high atom efficiency, and high regioselectivity. Additionally, it exhibits a broad substrate scope, enabling the synthesis of a range of arylacetic acid derivatives. Furthermore, this method can also be applied to the etherification of arylthiol derivatives, facilitating the preparation of various thiolated products, which would enhance the applicability and potential utility of this method in organic synthesis.