Palladium-Catalyzed Regioselective 5-exo-O-Cyclization/Oxidative Heck Cascades from o-Alkynylbenzamides and Electron-Deficient Alkenes

被引：27
作者：
Madich, Youssef [1 ,2 ]
Alvarez, Rosana [3 ]
Aurrecoechea, Jose M. [1 ]
机构：
[1] Univ Pais Vasco UPV EHU, Dept Quim Organ 2, Fac Ciencia & Tecnol, Bilbao 48080, Spain
[2] Univ Cadi Ayyad, Fac Sci & Tech Marrakech, Lab Chim Bioorgan & Macromol, Marrakech, Morocco
[3] Univ Vigo, Fac Quim, Dept Quim Organ, Vigo 36310, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 28期
关键词：
Homogeneous catalysis; Palladium; Cyclization; Cross-coupling; Regioselectivity; Oxygen heterocycles; INTRAMOLECULAR CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; ONE-POT; ALKYNES; ACCESS; ISOCOUMARINS;
D O I：
10.1002/ejoc.201402709
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Pd-catalyzed 5-exo-selective oxycyclization/oxidative Heck coupling cascade is described, starting from readily available ortho-alkynylbenzamides and functionalized olefins. The key to a high regioselectivity in the cyclization step is the choice of catalyst and/or additives. Thus, Pd(OAc)(2) provides the desired 5-exo products predominantly, whereas with PdCl2 or Pd(TFA)(2), the corresponding 6-endo products prevail. The subsequent oxidative Heck-type coupling takes place stereoselectively with the very predominant formation of E isomers, leading to an effective preparation of structurally diverse carbonyl-substituted allylideneisobenzofuranimines.
引用
收藏
页码：6263 / 6271
页数：9
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