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铃木反应作为合成一种新型用作液晶掺杂剂的阻转异构联苯衍生物关键步骤的应用。

Application of the Suzuki reaction as the key step in the synthesis of a novel atropisomeric biphenyl derivative for use as a liquid crystal dopant.

作者信息

Cammidge Andrew N, Crépy Karen V L

机构信息

Wolfson Materials and Catalysis Centre, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, United Kingdom.

出版信息

J Org Chem. 2003 Aug 22;68(17):6832-5. doi: 10.1021/jo034652s.

DOI:10.1021/jo034652s
PMID:12919061
Abstract

A heavily functionalized atropisomeric biphenyl derivative (4), which is designed to possess a large lateral dipole moment, has been synthesized with use of a Suzuki coupling as the key step and resolved by chiral HPLC. The final coupling reaction is complicated by rapid hydrolytic deboronation of the sterically hindered, electron poor boronate 22. Rigorously anhydrous conditions are therefore necessary to achieve the coupling.

摘要

一种高度官能化的阻转异构联苯衍生物（4）被合成出来，该衍生物设计为具有较大的侧向偶极矩，合成过程以铃木耦合反应作为关键步骤，并通过手性高效液相色谱法拆分。由于空间位阻大、电子匮乏的硼酸酯22发生快速水解脱硼反应，使得最终的耦合反应变得复杂。因此，需要严格的无水条件来实现耦合反应。

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