Palladium-Catalyzed Alkynylthiolation of Alkynes with Triisopropylsilylethynyl Sulfide

被引:23
作者
Iwasaki, Masayuki [1 ,2 ]
Fujino, Daishi [1 ,2 ]
Wada, Tatsuya [2 ]
Kondoh, Azusa [2 ]
Yorimitsu, Hideki [1 ,2 ]
Oshima, Koichiro [2 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
关键词
addition; alkynyl sulfide; alkynylthiolation; enyne; palladium; ARYLKETENE DITHIOACETAL MONOXIDES; PUMMERER REACTION; SULFONIUM SALTS; CARBON-CARBON; CYCLIZATION; BOND; CARBOTHIOLATION; HETEROCYCLES; HETEROATOM; INSERTION;
D O I
10.1002/asia.201100643
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Regio- and stereoselective addition of a silyl-substituted alkynyl sulfide to various terminal alkynes proceeds in the presence of a palladium catalyst to give (Z)-1-thio-1,3-enynes, which are useful building blocks for the synthesis of polysubstituted 1,3-enynes. Addition to internal alkynes also takes place under solvent-free conditions (see scheme). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:3190 / 3194
页数:5
相关论文
共 52 条
[1]   Recent advances in Pummerer reactions [J].
Akai, Shuji ;
Kita, Yasuyuki .
SULFUR-MEDIATED REARRANGEMENTS I, 2007, 274 :35-76
[2]   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 [J].
Ananikov, Valentine P. ;
Orlov, Nikolay V. ;
Kabeshov, Mikhail A. ;
Beletskaya, Irina P. ;
Starikova, Zoya A. .
ORGANOMETALLICS, 2008, 27 (16) :4056-4061
[3]  
[Anonymous], 2010, ANGEW CHEM
[4]   Transition-metal-catalyzed synthesis of organosulfur compounds [J].
Arisawa, Mieko ;
Yamaguchi, Masahiko .
PURE AND APPLIED CHEMISTRY, 2008, 80 (05) :993-1003
[5]   Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes [J].
Arisawa, Mieko ;
Igarashi, Yui ;
Tagami, Yoko ;
Yamaguchi, Masahiko ;
Kabuto, Chizuko .
TETRAHEDRON LETTERS, 2011, 52 (08) :920-922
[6]   Chemical transformations induced by triflic anhydride [J].
Baraznenok, IL ;
Nenajdenko, VG ;
Balenkova, ES .
TETRAHEDRON, 2000, 56 (20) :3077-3119
[7]   Element-element addition to alkynes catalyzed by the group 10 metals [J].
Beletskaya, I ;
Moberg, C .
CHEMICAL REVIEWS, 1999, 99 (12) :3435-3461
[8]   The Pummerer reaction: Methodology and strategy for the synthesis of heterocyclic compounds [J].
Bur, SK ;
Padwa, A .
CHEMICAL REVIEWS, 2004, 104 (05) :2401-2432
[9]   THIO-CLAISEN REARRANGEMENTS OF DIMETHYLALLYL 2-INDOLYL SULPHONIUM SALTS - POSSIBLE IMPLICATIONS IN INDOLE ALKALOID BIOSYNTHESIS [J].
BYCROFT, BW ;
LANDON, W .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (16) :967-&
[10]  
ElAli B., 2002, HDB ORGANOPALLADIUM