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Microwave‐Assisted Metal‐Free Decarboxylative Iodination/Bromination of Isoxazole‐4‐carboxylic Acids
Author(s) -
Barak Dinesh S.,
Dahatonde Dipak J.,
Batra Sanjay
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900572
Subject(s) - isoxazole , halogenation , chemistry , sonogashira coupling , decarboxylation , n bromosuccinimide , organic chemistry , combinatorial chemistry , palladium , catalysis
A microwave‐assisted metal‐free route to substituted 4‐haloisoxazoles via decarboxylative halogenation of substituted isoxazole‐4‐carboxylic acids using N ‐iodosuccinimide (NIS) and N ‐bromosuccinimide (NBS) in the presence of K 3 PO 4 is described. It was discovered that the substitutions present at the 3‐position of differently 3,5‐disubstituted isoxazoles influenced the outcome of the protocol. The methodology is compatible for performing decarboxylative halogenation followed by decarboxylative Suzuki‐Miyaura and Sonogashira couplings as one‐pot process.