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钯催化的 2-氯乙酸酯和 2-氯乙酰胺的α-芳基化反应。

Palladium-catalyzed α-arylation of 2-chloroacetates and 2-chloroacetamides.

机构信息

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.

出版信息

J Org Chem. 2013 Apr 19;78(8):4123-31. doi: 10.1021/jo400488q. Epub 2013 Apr 9.

DOI:10.1021/jo400488q
PMID:23570264
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3668638/
Abstract

A method has been developed for the Pd-catalyzed synthesis of α-(hetero)aryl esters and amides through a Suzuki-Miyaura cross-coupling reaction. This method avoids the use of strong base, does not necessitate inert or low temperature formation of reagents, and does not require the use of a large excess of organometallic reagent. Utilization of organotrifluoroborate salts as nucleophilic partners allows a variety of functional groups and heterocyclic compounds to be tolerated.

摘要

已经开发出一种通过钯催化的 Suzuki-Miyaura 交叉偶联反应合成 α-(杂)芳基酯和酰胺的方法。该方法避免了强碱的使用,不需要在惰性或低温下形成试剂,也不需要使用大量的有机金属试剂。利用有机三氟硼酸盐作为亲核试剂可以容忍各种官能团和杂环化合物。

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本文引用的文献

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Organotrifluoroborate hydrolysis: boronic acid release mechanism and an acid-base paradox in cross-coupling.有机三氟硼酸盐的水解:交叉偶联中的硼酸释放机制和酸碱悖论。
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Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User's Guide.钯催化胺化反应中的二烷基联芳基膦:用户指南
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Direct use of dioxygen as an oxygen source: catalytic oxidative synthesis of amides.直接使用氧气作为氧源:酰胺的催化氧化合成。
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Palladium-catalyzed cross-coupling of sterically demanding boronic acids with α-bromocarbonyl compounds.钯催化的空间位阻硼酸与α-溴代羰基化合物的交叉偶联反应。
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Synthesis of α-aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates.通过钯催化氰基乙酸盐与芳基卤化物及三氟甲磺酸盐的脱羧偶联反应合成α-芳基腈
Angew Chem Int Ed Engl. 2011 May 2;50(19):4470-4. doi: 10.1002/anie.201006763. Epub 2011 Apr 6.
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