Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent
Oxidative Biaryl Coupling Reaction of Phenol Ether Derivatives Using a Hypervalent Iodine(III) Reagent
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DOI：
10.1021/jo980704f
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发表时间：
1998-10
影响因子：
3.6
通讯作者：
T. Takada;M. Arisawa;M. Gyoten;Ryuji Hamada;H. Tohma;Y. Kita
中科院分区：
文献类型：
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作者：
T. Takada;M. Arisawa;M. Gyoten;Ryuji Hamada;H. Tohma;Y. Kita
研究了高价碘(III)诱导的酚醚衍生物(非酚衍生物)的分子内联芳偶联反应，旨在制备各种二苯并杂环化合物。 1,3-二芳基丙烷 (1a−e)、N-苄基-N-苯乙胺 (2a−c) 和 N,N-二苄胺 (3a−e) 与含有 BF3·Et2O 的高价碘试剂苯碘 (III) 双(三氟乙酸酯) (PIFA) 在 CH2Cl2 中反应，以良好的收率得到联芳基偶联产物 (4−6)。作为该反应的应用，我们研究了含氧和硫的二苯并杂环化合物（12−15）的合成，其侧链部分可以通过已知方法轻松裂解，得到2,2'-取代的联苯化合物（16−18）。
The hypervalent iodine(III)-induced intramolecular biaryl coupling reaction of phenol ether derivatives (nonphenolic derivatives) was investigated with the aim of preparing various dibenzo heterocyclic compounds. 1,3-Diarylpropanes (1a−e), N-benzyl-N-phenethylamines (2a−c) and N,N-dibenzylamines (3a−e) react with a hypervalent iodine reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA), containing BF3·Et2O in CH2Cl2 to give the biaryl coupling products (4−6) in good yield. As an application of the reaction, we examined the synthesis of oxygen- and sulfur-containing dibenzoheterocyclic compounds (12−15), whose side chain moiety could be easily cleaved by the known method to give 2,2‘-substituted biphenyl compounds (16−18).