Transition-metal-catalyzed regioselective aroyl- and trifluoro-acetylthiolation of alkynes using thioesters

被引:38
作者
Minami, Yasunori [1 ]
Kuniyasu, Hitoshi [1 ]
Miyafuji, Kiyoshi [1 ]
Kambe, Nobuaki [1 ]
机构
[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan
关键词
ADDITION-REACTIONS; COMPLEXES; RHODIUM; INSERTION; PLATINUM; SULFIDES; BOND; HYDROSILYLATION; DECARBONYLATION; 1,3-DIENES;
D O I
10.1039/b900492k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Intermolecular CO-retained carbothiolation of alkynes using thioesters took place to afford beta-SR substituted enone derivatives; the choice of catalyst (Pd(dba)(2)-dppe) and the introduction of a CF3 group into the thioesters are the key to achieving the transformation.
引用
收藏
页码:3080 / 3082
页数:3
相关论文
共 30 条
  • [1] Stereodefined synthesis of a new type of 1,3-dienes by ligand-controlled carbon-carbon and carbon-heteroatom bond formation in nickel-catalyzed reaction of diaryldichalcogenides with Alkynes
    Ananikov, Valentine P.
    Orlov, Nikolay V.
    Kabeshov, Mikhail A.
    Beletskaya, Irina P.
    Starikova, Zoya A.
    [J]. ORGANOMETALLICS, 2008, 27 (16) : 4056 - 4061
  • [2] BACKVALL JE, 1994, J ORG CHEM, V59, P5850
  • [3] HYDROSILYLATION OF 1-PENTYNE BY TRIETHYLSILANE CATALYZED BY PHOSPHINE-RHODIUM COMPLEXES
    BRADY, KA
    NILE, TA
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 206 (03) : 299 - 304
  • [4] Palladium-catalyzed thioesterification of alkynes with O-methyl S-phenyl thiocarbonate
    Hua, R
    Takeda, H
    Onozawa, SY
    Abe, Y
    Tanaka, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (12) : 2899 - 2900
  • [5] Rhodium-catalyzed nondecarbonylative addition reaction of ClCOCOOC2H5 to alkynes
    Hua, RM
    Onozawa, SY
    Tanaka, M
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (12) : 3621 - 3630
  • [6] Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides
    Hua, Ruimao
    Takeda, Hideaki
    Onozawa, Shun-ya
    Abe, Yoshimoto
    Tanaka, Masato
    [J]. ORGANIC LETTERS, 2007, 9 (02) : 263 - 266
  • [7] Nickel-catalyzed decarbonylative addition of phthalimides to alkynes
    Kajita, Yuichi
    Matsubara, Seijiro
    Kurahashi, Takuya
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (19) : 6058 - +
  • [8] CO-retentive addition reactions of fluorinated acid chlorides to alkynes
    Kashiwabara, T
    Kataoka, K
    Hua, R
    Shimada, S
    Tanaka, M
    [J]. ORGANIC LETTERS, 2005, 7 (11) : 2241 - 2244
  • [9] Rhodium-Complex-Catalyzed Addition Reactions of Chloroacetyl Chlorides to Alkynes
    Kashiwabara, Taigo
    Fuse, Kouichiro
    Hua, Ruimao
    Tanaka, Masato
    [J]. ORGANIC LETTERS, 2008, 10 (23) : 5469 - 5472
  • [10] β-cis-SAr effect on decarbonylation from α,β-unsaturated acyl and aroyl complexes
    Kato, T
    Kuniyasu, H
    Kajiura, T
    Minami, Y
    Ohtaka, A
    Kinomoto, M
    Terao, J
    Kurosawa, H
    Kambe, N
    [J]. CHEMICAL COMMUNICATIONS, 2006, (08) : 868 - 870