Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides.
Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate is proposed on the basis of isolation of pi-allyl complexes and distribution of products in the reactions of alpha- or gamma-methylated allyl sulfide. [reaction: see text].
Hua
Ruimao
R
Department of Chemistry, Tsinghua University, Beijing 100084, China.
Takeda
Hideaki
H
Onozawa
Shun-ya
SY
Abe
Yoshimoto
Y
Tanaka
Masato
M
D000480:Alkynes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry*
D000480:Alkynes; D000498:Allyl Compounds; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D013440:Sulfides; D009532:Nickel