Copper-catalyzed thiolation annulations of 1,4-dihalides with sulfides leading to 2-trifluoromethyl benzothiophenes and benzothiazoles.
Copper-catalyzed double thiolation reaction of 1,4-dihalides with sulfides has been developed for selectively synthesizing 2-trifluoromethyl benzothiophenes and benzothiazoles. In the presence of CuI, a variety of 2-halo-1-(2-haloaryl)-3,3,3-trifluoropropylenes smoothly underwent the thiolation annulation with Na(2)S to afford 2-trifluoromethyl benzothiophenes in moderate to good yields. Moreover, the conditions are compatible with N-(2-haloaryl)trifluoroacetimidoyl chlorides in the presence of NaHS and K(3)PO(4), leading to 2-trifluoromethyl benzothiazoles.
Li
Chun-Lin
CL
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
Zhang
Xing-Guo
XG
Tang
Ri-Yuan
RY
Zhong
Ping
P
Li
Jin-Heng
JH
D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry*; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
D052160:Benzothiazoles; D013438:Sulfhydryl Compounds; D013440:Sulfides; D013876:Thiophenes; D003300:Copper