Regioselectivity in the Sonogashira coupling of 4,6-dichloro-2-pyrone

被引:43
作者
Fairlamb, IJS [1 ]
O'Brien, CT
Lin, ZY
Lam, KC
机构
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
[2] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1039/b518232h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Sonogashira cross-coupling of 4,6-dichloro-2-pyrone with terminal acetylenes proceeds in good yields and high regioselectivity for the 6-position; dibenzylidene acetone (dba) type ligands play a non-innocent role in reactions mediated by Pd(dba)(2)/PPh3; theoretical studies indicate that C-6 oxidative addition is favoured both kinetically and thermodynamically.
引用
收藏
页码:1213 / 1216
页数:4
相关论文
共 28 条
[11]   Halogenated-2-pyrones in Sonogashira cross-coupling:: limitations, optimisation and consequences for GC analysis of Pd-mediated reactions [J].
Fairlamb, IJS ;
Lee, AF ;
Loe-Mie, FEM ;
Niemelä, EH ;
O'Brien, CT ;
Whitwood, AC .
TETRAHEDRON, 2005, 61 (41) :9827-9838
[12]   η2-dba complexes of Pd(0):: The substituent effect in Suzuki-Miyaura coupling [J].
Fairlamb, IJS ;
Kapdi, AR ;
Lee, AF .
ORGANIC LETTERS, 2004, 6 (24) :4435-4438
[13]   η1-Bound 2-pyrone complexes of molybdenum and iron:: A synthetic and structural study [J].
Fairlamb, IJS ;
Lynam, JM ;
Taylor, IE ;
Whitwood, AC .
ORGANOMETALLICS, 2004, 23 (21) :4964-4969
[14]   2-Pyrones possessing antimicrobial and cytotoxic activities [J].
Fairlamb, IJS ;
Marrison, LR ;
Dickinson, JM ;
Lu, FJ ;
Schmidt, JP .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (15) :4285-4299
[15]   Synthesis of (Bromo-η4-2-pyrone)tricarbonyliron complexes [J].
Fairlamb, IJS ;
Syvänne, SM ;
Whitwood, AC .
SYNLETT, 2003, (11) :1693-1697
[16]   Palladium-catalysed alkynylations of 2-pyrone (pyran-2-one) halides [J].
Fairlamb, IJS ;
Lu, FJ ;
Schmidt, JP .
SYNTHESIS-STUTTGART, 2003, (16) :2564-2570
[17]  
FAIRLAMB IJS, UNPUB
[18]  
Kalinin VN, 1996, MENDELEEV COMMUN, P244
[19]   Regioselectivity in the Stille coupling reactions of 3,5-dibromo-2-pyrone [J].
Kim, WS ;
Kim, HJ ;
Cho, CG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14288-14289
[20]   Regioselective Stille coupling reactions of 3,5-dibromo-2-pyrone with various aryl and vinyl stannanes [J].
Kim, WS ;
Kim, HJ ;
Cho, CG .
TETRAHEDRON LETTERS, 2002, 43 (50) :9015-9017