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Practical Synthesis of α ‐Trifluoromethylated Pyridines Based on Regioselective Cobalt‐Catalyzed [2+2+2] Cycloaddition using Trifluoromethylated Diynes with Nitriles
Author(s) -
Kumon Tatsuya,
Yamada Shigeyuki,
Agou Tomohiro,
Fukumoto Hiroki,
Kubota Toshio,
Hammond Gerald B.,
Konno Tsutomu
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001433
Subject(s) - chemistry , regioselectivity , cycloaddition , cobalt , catalysis , zinc , bromide , substrate (aquarium) , zinc bromide , bipyridine , medicinal chemistry , combinatorial chemistry , organic chemistry , crystal structure , oceanography , geology
Regioselective cobalt‐catalyzed [2+2+2] cycloaddition using fluorine‐containing diynes with nitriles was described. Cycloaddition of fluorinated diynes with nitriles under the influence of CoCl 2 (phen), zinc bromide, and zinc dust in dichloroethane at 80 °C for 3 h took place smoothly, exclusively affording the corresponding α ‐fluoroalkylated pyridines in excellent yields. In addition, dinitriles as substrate were also found to be suitable for this reaction, giving the corresponding fluoroalkylated bipyridine derivatives in excellent yields.