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Libraries of C‐5 Substituted Imidazoles and Oxazoles by Sequential Van Leusen (VL)–Suzuki, VL–Heck and VL–Sonogashira in Imidazolium‐ILs with Piperidine‐Appended‐IL as Base
Author(s) -
Savanur Hemantkumar M.,
Kalkhambkar Rajesh G.,
Laali Kenneth K.
Publication year - 2018
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.201800804
Subject(s) - chemistry , sonogashira coupling , piperidine , oxazole , suzuki reaction , combinatorial chemistry , organic chemistry , palladium , catalysis
Facile access to diverse C5‐substituted imidazoles and oxazoles via sequential Van Leusen–Suzuki, Van Leusen–Heck, and Van Leusen–Sonogashira protocols, employing imidazolium‐ILs as solvents along with piperidine‐appended imidazolium [PAIM][NTf 2 ] as task‐specific basic IL has been demonstrated, in a high‐yielding one‐pot method, starting with readily available aldimines (for imidazole) or aldehydes (for oxazole) and tosylmethylisocyanide (Tos‐MIC), under mild conditions with potential for recycling and reuse of the IL solvent. The scope of the method is supported 49 examples.