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Synthesis of novel halopyridinylboronic acids and esters. Part 4: Halopyridin-2-yl-boronic acids and esters are stable, crystalline partners for classical Suzuki cross-coupling
Tetrahedron ( IF 2.1 ) Pub Date : 8 December 2003 , DOI: 10.1016/j.tet.2003.10.020
Alexandre Bouillon , Jean-Charles Lancelot , Jana Sopkova de Oliveira Santos , Valérie Collot , Philipppe R Bovy , Sylvain Rault

This paper describes some methods for the synthesis and the isolation of novel 5 or 6-halopyridin-2-yl-boronic acids and esters 3, 4, 7. These compounds are prepared via a regioselective halogen–metal exchange using n-butyllithium and subsequent quenching with triisopropylborate starting from appropriate dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pd-catalysed coupling with arylhalides and authorise a strategy to produce new pyridines libraries.

中文翻译:

新型卤代吡啶基硼酸和酯的合成。第4部分:卤代吡啶-2-基硼酸和酯是稳定的晶体伴侣,可用于经典的铃木交叉偶联

本文描述了用于合成一些方法和新颖的5或6-卤代吡啶-2-基-硼酸和酯隔离347。这些化合物是通过使用丁基锂进行区域选择性的卤素-金属交换并随后从适当的二卤代吡啶开始用三异丙基硼酸酯淬灭来制备的。迄今为止研究的所有底物均提供单一的区域异构硼酸或酯产物。另外,已经发现这些化合物与芳基卤化物经历了Pd催化的偶联,并授权了一种制备新吡啶库的策略。
更新日期:2017-01-31
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