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Efficient and Rapid Regioselective One‐Pot Synthesis of 1,4‐Disubstituted 1,2,3‐Triazoles from In Situ Generated Potassium Arylethynyltrifluoroborates through Sonogashira Reaction
Author(s) -
Song Jung Ho,
Choi Pilju,
Lee Seung Eon,
Jeong Kyu Hyuk,
Kim Taejung,
Kang Ki Sung,
Choi Yong Soo,
Ham Jungyeob
Publication year - 2013
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.201301003
Subject(s) - chemistry , sonogashira coupling , regioselectivity , potassium , aryl , halide , medicinal chemistry , stoichiometry , potassium fluoride , aqueous solution , combinatorial chemistry , organic chemistry , palladium , catalysis , inorganic chemistry , fluoride , alkyl
Potassium arylethynyltrifluoroborates, the intermediates generated by the Sonogashira reaction of potassium ethynyltrifluoroborate with various aryl halides, were directly coupled with azides in the presence of a stoichiometric amount of CuI under aqueous conditions, and the desired 1,4‐disubstituted 1,2,3‐triazoles were isolated in good yields. Both electron‐donating and electron‐withdrawing substituents on the potassium arylethynyltrifluoroborates gave moderate to excellent yields of the isolated products.