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使用三异丙基硼酸锂的 Suzuki-Miyaura 偶联反应的一般方法。

A general method for Suzuki-Miyaura coupling reactions using lithium triisopropyl borates.

机构信息

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

出版信息

Org Lett. 2012 Sep 7;14(17):4606-9. doi: 10.1021/ol302063g. Epub 2012 Aug 15.

DOI:10.1021/ol302063g
PMID:22894743
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3684691/
Abstract

Conditions for the Suzuki-Miyaura coupling of lithium triisopropyl borates are reported, as well as a procedure for a one-pot lithiation, borylation, and subsequent Suzuki-Miyaura coupling of various heterocycles with aryl halides. These borate species are much more stable toward protodeboronation than the corresponding boronic acids and can conveniently be stored on benchtop at room temperature.

摘要

报告了三异丙基硼酸锂与Suzuki-Miyaura 偶联的条件，以及一种一锅法锂化、硼酸化和随后与各种杂环芳烃卤化物进行 Suzuki-Miyaura 偶联的方法。这些硼酸酯比相应的硼酸稳定得多，不容易发生脱硼反应，方便在室温下在实验台上储存。

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Angew Chem Int Ed Engl. 2011 Nov 4;50(45):10665-9. doi: 10.1002/anie.201105223. Epub 2011 Sep 20.
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A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.一种新型钯前催化剂可实现不稳定的多氟代苯基和 2-杂芳基硼酸的快速铃木-宫浦偶联反应。
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Sterically demanding trialkylphosphines for palladium-catalyzed cross coupling reactions-alternatives to PtBu3.空间位阻要求高的三烷基膦在钯催化交叉偶联反应中的应用——替代 PtBu3。
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Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.三氟硼酸盐和单配位钯配合物作为催化剂——Suzuki-Miyaura 偶联的完美组合。
Angew Chem Int Ed Engl. 2009;48(49):9240-61. doi: 10.1002/anie.200904306.
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A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.不稳定硼酸的通用解决方案：从空气稳定的MIDA硼酸酯进行缓释交叉偶联。
J Am Chem Soc. 2009 May 27;131(20):6961-3. doi: 10.1021/ja901416p.
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