One-pot synthesis of amine-substituted aryl sulfides and benzo[b]thiophene derivatives.
A series of amine-substituted aryl sulfides have been synthesized from nitroaryl halides via a simple one-pot procedure involving metal-free C-S cross-coupling and in situ nitro group reduction. Various nitroaryl halides were reacted with thiols in recyclable poly(ethylene glycol) to afford the amine-substituted aryl sulfides in high yield. Additionally, the cross-coupling reactions of nitro- and aldehyde-substituted aryl halides with benzyl thiols under the same reaction conditions were demonstrated to afford benzothiazole and phenylbenzo[b]thiophene derivatives.
Duan
Zhongyu
Z
Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543.
Ranjit
Sadananda
S
Liu
Xiaogang
X
D000588:Amines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
D000588:Amines; D013440:Sulfides; D013876:Thiophenes; C088015:benzothiophene