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Modular Synthesis of Multisubstituted Furans through Palladium‐Catalyzed Three‐Component Condensation of Alkynylbenziodoxoles, Carboxylic Acids, and Imines
Author(s) -
Wu Junliang,
Yoshikai Naohiko
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201504687
Subject(s) - furan , chemistry , palladium , catalysis , condensation , organic chemistry , combinatorial chemistry , carboxylic acid , modular design , computer science , physics , thermodynamics , operating system
Mild and regiocontrolled synthesis of a multisubstituted furan is achieved through Pd(OAc) 2 ‐catalyzed room‐temperature condensation of an alkynylbenziodoxole, a carboxylic acid, and an enolizable ketimine, which contribute to C1, CO, and C2 fragments, respectively, to the furan skeleton. The reaction tolerates a broad range of functional groups in each of the reaction components, and enables highly modular and flexible synthesis of variously substituted furans. The reaction is particularly effective for the rapid generation of tri‐ and tetraarylfurans and furan‐containing oligoarylenes without relying on conventional cross‐coupling chemistry.