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本文引用的文献

1
Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.三氟硼酸钾盐作为用于困难烷基转移反应的便捷、稳定试剂。
Curr Opin Drug Discov Devel. 2009 Nov;12(6):811-23.
2
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.
3
Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.杂芳基三氟硼酸钾的铃木-宫浦交叉偶联反应的范围
J Org Chem. 2009 Feb 6;74(3):973-80. doi: 10.1021/jo802590b.
4
Cobalt(II)-catalyzed regio- and stereoselective hydroarylation of alkynes with organoboronic acids.钴(II)催化炔烃与有机硼酸的区域和立体选择性氢芳基化反应。
Chemistry. 2008;14(36):11296-9. doi: 10.1002/chem.200801858.
5
A simple and modular strategy for small molecule synthesis: iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks.一种用于小分子合成的简单且模块化的策略:B-保护的卤代硼酸砌块的迭代铃木-宫浦偶联反应。
J Am Chem Soc. 2007 May 30;129(21):6716-7. doi: 10.1021/ja0716204. Epub 2007 May 9.
6
Highly efficient monophosphine-based catalyst for the palladium-catalyzed suzuki-miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters.用于钯催化杂芳基卤化物与杂芳基硼酸及酯的铃木-宫浦反应的高效单膦基催化剂。
J Am Chem Soc. 2007 Mar 21;129(11):3358-66. doi: 10.1021/ja068577p. Epub 2007 Feb 28.
7
Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives: a one-pot protocol to substituted azabiaryls.吡啶衍生物的定向邻位金属化-硼化反应及铃木-宫浦交叉偶联反应:一种合成取代氮杂联芳基化合物的一锅法
J Org Chem. 2007 Mar 2;72(5):1588-94. doi: 10.1021/jo0620359. Epub 2007 Feb 7.
8
Palladium-catalyzed cross-coupling reactions in total synthesis.钯催化交叉偶联反应在全合成中的应用
Angew Chem Int Ed Engl. 2005 Jul 18;44(29):4442-89. doi: 10.1002/anie.200500368.
9
Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions.铑催化的不对称1,4-加成及其相关的不对称反应。
Chem Rev. 2003 Aug;103(8):2829-44. doi: 10.1021/cr020022z.
10
Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates.烯基三氟硼酸钾的铃木-宫浦交叉偶联反应
J Org Chem. 2002 Nov 29;67(24):8424-9. doi: 10.1021/jo026236y.

DABO硼酸酯:用于铃木-宫浦交叉偶联反应的稳定杂环硼酸配合物

DABO Boronates: Stable Heterocyclic Boronic Acid Complexes for Use in Suzuki-Miyaura Cross-Coupling Reactions.

作者信息

Reilly Maureen K, Rychnovsky Scott D

机构信息

1102 NSII, Department of Chemistry, University of California, Irvine. Irvine, CA 92697-2025.

出版信息

Synlett. 2011 Oct 1;2011(16). doi: 10.1055/s-0030-1261218.

DOI:10.1055/s-0030-1261218
PMID:24371372
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3870905/
Abstract

Diethanolamine complexed heterocyclic boronic acids (DABO boronates) are air-stable reagents that can be used directly in Suzuki-Miyaura reactions in the presence of water or a protic co-solvent. Interestingly, heterocyclic DABO boronates can be stored for extended periods of time at room temperature with no noticeable degradation, unlike their boronic acid counterparts. Heterocyclic DABO boronates constitute an operationally simple and efficient alternative to other boronic acid derivatives as coupling partners in palladium catalyzed cross-coupling reactions under standard Suzuki-Miyaura conditions.

摘要

二乙醇胺络合的杂环硼酸酯(DABO硼酸酯)是空气稳定的试剂,可在水或质子性共溶剂存在下直接用于铃木-宫浦反应。有趣的是,与硼酸类似物不同,杂环DABO硼酸酯可以在室温下长时间储存而无明显降解。在标准铃木-宫浦条件下,杂环DABO硼酸酯作为钯催化交叉偶联反应中的偶联伙伴,是其他硼酸衍生物在操作上简单且高效的替代品。