Palladium-catalyzed sequential alkylation-alkenylation reactions. Application to the synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines

被引：63

作者：

Lautens, M ^{[1
]}

Paquin, JF ^{[1
]}

Piguel, S ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Labs, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 11期

关键词：

Intramolecular Heck sequence;

D O I：

10.1021/jo025730z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 2-substituted-4-benzoxepines and 2,5-disubstituted-4-benzoxepines from aryl iodides and bromoenoates is described. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the reaction conditions (Pd(OAc)(2) (10 mol %), tri-2-furylphosphine (20 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, 85 degreesC), moderate to excellent yields of benzoxepines bearing numerous substituents (Me, F, Cl, etc.) are obtained.

引用

页码：3972 / 3974

页数：3

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