Synthesis of Complex ortho-Allyliodoarenes by Employing the Reductive Iodonio-Claisen Rearrangement

被引：44

作者：

Khatri, Hem Raj ^{[1
,2
]}

Zhu, Jianglong ^{[1
,2
]}

机构：

[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA

[2] Univ Toledo, Sch Green Chem & Engn, Toledo, OH 43606 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 39期

关键词：

allylation; aryl iodide; hypervalent compounds; iodine; pericyclic reaction; rearrangement; OXY-COPE REARRANGEMENTS; POLYVALENT IODINE COMPOUNDS; ORGANIC-SYNTHESIS; DERIVATIVES; REAGENTS; DEAROMATIZATION; SELECTIVITY; ALLYLATION; PRECURSORS; CHEMISTRY;

D O I：

10.1002/chem.201202049

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reductive iodonio-Claisen rearrangement (RICR), involving complex aromatic λ 3-iodanes and allyltrimethylsilane, was investigated. The RICR reaction of complex substituted aromatic hypervalent iodine (III) compounds and an allylmetal partner was conducted. The anionic oxy Cope rearrangement was found to be approximately 10 10 to 10 17 times faster than the neutral oxy Cope rearrangement due to weakening of the adjacent C-C bond by the oxygen anion. The results also indicate that the steric and electronic nature of the aromatic λ 3-iodanes is the dominant factor influencing the [3,3]-sigmatropic rearrangement reaction. The removal of tert-butyl ether protecting group by using trifluroacetic acid in dichloromethane in the presence of triisopropylsilane gives the natural product broussin in 39% yield.

引用

页码：12232 / 12236

页数：5

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