Application of iodanes to the dimerization of terminal alkynes

被引:25
作者
Yan, Jie [1 ]
Lin, Feng
Yang, Zhenping
机构
[1] Zhejiang Univ Technol, Coll Chem Engn & Mat Sci, Hangzhou 310032, Zhejiang, Peoples R China
[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源
SYNTHESIS-STUTTGART | 2007年 / 09期
关键词
dimerization; diyne; iodane; (diacetoxyiodo)benzene; iodosylbenzene;
D O I
10.1055/s-2007-966008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The dimerization of terminal acetylenes was Studied using iodanes as oxidants under palladium-catalyzed conditions. It was found that a number of iodanes were useful in the reaction, with (diacetoxyiodo)benzene and iodosylbenzene being the best oxidants. Diynes were prepared in the dimerization in good yields in a short period of time at room temperature.
引用
收藏
页码:1301 / 1303
页数:3
相关论文
共 36 条
[1]   STRUCTURE OF O-IODOSOBENZOIC ACID AND OF CERTAIN DERIVATIVES [J].
BAKER, GP ;
MANN, FG ;
SHEPPARD, N ;
TETLOW, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1965, (JUN) :3721-&
[2]   A PROCEDURE FOR THE OXIDATIVE DIMERIZATION OF ALIPHATIC 1-ALKYNES [J].
BRANDSMA, L ;
VERKRUIJSSE, HD ;
WALDA, B .
SYNTHETIC COMMUNICATIONS, 1991, 21 (01) :137-139
[3]   Palladium-catalyzed homocoupling reaction of 1-iodoalkynes: A simple and efficient synthesis of symmetrical 1,3-diynes [J].
Damle, SV ;
Seomoon, D ;
Lee, PH .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7085-7087
[4]   Pd-catalysed cross coupling of terminal alkynes to diynes in the absence of a stoichiometric additive [J].
Fairlamb, IJS ;
Bäuerlein, PS ;
Marrison, LR ;
Dickinson, JM .
CHEMICAL COMMUNICATIONS, 2003, (05) :632-633
[5]   Cyclic diaryliodonium ions: old mysteries solved and new applications envisaged [J].
Grushin, VV .
CHEMICAL SOCIETY REVIEWS, 2000, 29 (05) :315-324
[6]  
HARA H, 1992, TETRAHEDRON LETT, V34, P6419
[7]  
HAS AS, 1962, J ORG CHEM, V27, P3320
[8]  
HUNSTMAN VD, 1978, CHEM CARBON CARBON T, P553
[9]   HYPERVALENT ORGANOIODINE - REACTIONS OF SILVER ARYLSULFONATES WITH IODOSOBENZENE DICHLORIDE [J].
KOSER, GF ;
WETTACH, RH .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (08) :1476-1478
[10]   Transmetalation of palladium enolate and its application in palladium-catalyzed homocoupling of alkynes: A room-temperature, highly efficient route to make diynes [J].
Lei, AW ;
Srivastava, M ;
Zhang, XM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1969-1971