Synthesis of alkenyl sulfides through the iron-catalyzed cross-coupling reaction of vinyl halides with thiols.
We report here the iron-catalyzed cross-coupling reaction of alkyl vinyl halides with thiols. While many works are devoted to the coupling of thiols with alkyl vinyl iodides, interestingly, the known S-vinylation of vinyl bromides and chlorides is limited to 1-(2-bromovinyl)benzene and 1-(2-chlorovinyl)benzene. Investigation on the coupling reaction of challenging alkyl vinyl bromides and chlorides with thiols is rare. Since the coupling of 1-(2-bromovinyl)benzene and 1-(2-chlorovinyl)benzene with thiols can be performed in the absence of any catalyst, here we focus on the coupling of thiols with alkyl vinyl halides. This system is generally reactive for alkyl vinyl iodides and bromides to provide the products in good yields. 1-(Chloromethylidene)-4-tert-butyl-cyclohexane was also coupled with thiols, giving the targets in moderate yields.
Department of Chemistry, National Chung Hsing University, Taichung, Taiwan 402, ROC.
Yun-Yung
YY
Lin
Yu-Jen
YJ
Wang
Che-Hung
CH
Lin
Jun-Hao
JH
Cheng
Chin-Fa
CF
Lee
D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D005290:Ferric Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D002712:Chlorides; D003432:Cross-Linking Reagents; D005290:Ferric Compounds; D013438:Sulfhydryl Compounds; D013440:Sulfides; D014753:Vinyl Compounds; C024555:ferric chloride