Chemoselective Suzuki Coupling of Bromoarenes Catalysed by Palladium(II)‐Complexing Macrocycles in Aqueous Media,ChemistrySelect

当前位置： X-MOL 学术 › ChemistrySelect › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Chemoselective Suzuki Coupling of Bromoarenes Catalysed by Palladium(II)‐Complexing Macrocycles in Aqueous Media
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-01-09 , DOI: 10.1002/slct.201703073
Masahiro Ogawa ₁ , Hiromitsu Sogawa ₁ , Shunya Mizuno ₁ , Daisuke Aoki ₁ , Toshikazu Takata ₁

Affiliation

Palladium‐complexing macrocyclic catalysts efficiently and chemoselectively catalysed the Suzuki coupling reaction of bromoarenes. Bromobenzene and 2‐bromopyridine were efficiently monoarylated with 4‐methoxyphenylboronic acid when catalysed by macrocyclic catalysts comprising cyclic pyridine‐2,6‐bisamide pincer‐type ligands with palladium (II) located in the inner cavity (PdMCs). The Suzuki coupling of 2,6‐dibromopyridine to aryl boronic acids catalysed by PdMCs afforded the corresponding monoarylpyridines with high selectivity and yield, whereas a mixture of mono‐ and di‐arylpyridines was obtained when palladium chloride was used as the catalyst. Interestingly, the chemoselectivity increased as the cavity size of the PdMCs decreased. The high chemoselectivity seemed to arise from the steric effect of the macrocyclic ligand. Moreover, an unsymmetrical 2,6‐diarylpyridine was successfully synthesised in high yield by two sequential couplings employing PdMCs followed by palladium chloride.

中文翻译：

钯（II）络合大环化合物在水介质中催化溴代芳烃的化学选择性铃木偶联

钯络合的大环催化剂可高效，化学选择性地催化溴代芳烃的Suzuki偶联反应。当溴环和2-溴代吡啶被内含钯（II）的大环催化剂与位于内腔（PdMCs）的大环催化剂催化时，可被4-甲氧基苯基硼酸有效地单芳基化。PdMCs催化2,6-二溴吡啶与芳基硼酸的Suzuki偶联提供了高选择性和高收率的相应单芳基吡啶，而当使用氯化钯作为催化剂时，则获得了单芳基吡啶和二芳基吡啶的混合物。有趣的是，化学选择性随着PdMC腔尺寸的减小而增加。高的化学选择性似乎是由于大环配体的空间效应引起的。而且，

更新日期：2018-01-09

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11