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Scalable Multicomponent Synthesis of (Hetero)aryl‐Substituted Phenyls: Focus on Metal‐Free Halogenated Biaryls, 3‐Arylindoles, and Isourolithine A Synthesis
Author(s) -
Temperini Andrea,
Lanari Daniela,
Colognese Francesco,
Piazzolla Francesca
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901551
Subject(s) - chemistry , aryl , regioselectivity , context (archaeology) , alkyne , combinatorial chemistry , organic chemistry , scalability , catalysis , computer science , database , alkyl , paleontology , biology
In the context of the growing interest of the scientific community for the development of sustainable synthetic strategies to access aromatic structures, we present a practical and metal‐free approach to (hetero)biaryls which exploits the advantages of multicomponent reactions in sustainable solvents. In situ acid‐catalysed generation of (hetero)aryl acetoxy dienes from the corresponding (hetero)arylidene acetones in a metal vessel, followed by Diels‐Alder reaction using an electron‐poor alkyne as dienophile, delivers the expected aromatic products after final oxidation of the cycloadduct. This protocol has been demonstrated as a convenient alternative to the previously reported synthetic strategies, considering its scalability and environmental sustainability and the low cost of substrates and equipment. Moreover, it has been successfully applied to the metal‐free regioselective synthesis of (hetero)aryl‐substituted‐phenyls, 2‐unsubstituted‐3‐aryl‐indoles, and to the total synthesis of isourolithine A.