Heck coupling with nonactivated alkenyl tosylates and phosphates: Examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates

被引:167
作者
Hansen, Anders L.
Ebran, Jean-Philippe
Ahlquist, Marten
Norrby, Per-Ola
Skrydstrup, Troels
机构
[1] Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark
[2] Univ Aarhus, inSPIN, Ctr Insoluble Prot Struct, Dept Chem, DK-8000 Aarhus, Denmark
[3] Univ Aarhus, Nanosci Ctr, DK-8000 Aarhus, Denmark
关键词
1,2-migration; alkenes; Heck reaction; phosphates; tosylates;
D O I
10.1002/anie.200600442
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron-deficient olefins. An unexpected 1,2-migration of the alkenyl Pd II intermediates (see Scheme) leads to the isomerized Heck coupling product. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3349 / 3353
页数:5
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