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铁催化的烷基亲电试剂的硼化反应。

Iron-catalyzed borylation of alkyl electrophiles.

机构信息

Department of Chemistry, Indiana University , 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States.

出版信息

J Am Chem Soc. 2014 Jul 9;136(27):9521-3. doi: 10.1021/ja505199u. Epub 2014 Jun 23.

Abstract

The use of low-cost iron(III) acetoacetate (Fe(acac)3) and tetramethylethylenediamine (TMEDA) enables the direct cross-coupling of alkyl halides with bis(pinacolato)diboron. This approach allows for the borylation of activated or unactivated primary, secondary, and tertiary bromides. Moreover, even the borylation of benzylic or allylic chlorides, tosylates, and mesylates are possible. The reactions proceed under mild conditions at room temperature and show broad functional-group compatibility and "robustness" as measured by a modified Glorius robustness screen.

摘要

使用廉价的乙酰丙酮铁(III)(Fe(acac)3)和四甲基乙二胺(TMEDA)可以实现卤代烷与双(频哪醇)二硼的直接交叉偶联。这种方法允许对伯、仲和叔溴化物进行硼化。此外,甚至苄基或烯丙基氯化物、对甲苯磺酸盐和甲磺酸盐的硼化也是可能的。反应在温和条件下于室温下进行,并表现出广泛的官能团相容性和“鲁棒性”,这可以通过改良的 Glorius 鲁棒性筛选来衡量。

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