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通过铱催化芳烃的硼化反应一锅法合成芳基硼酸和芳基三氟硼酸盐。

One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes.

作者信息

Murphy Jaclyn M, Tzschucke C Christoph, Hartwig John F

机构信息

Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, USA.

出版信息

Org Lett. 2007 Mar 1;9(5):757-60. doi: 10.1021/ol062903o. Epub 2007 Feb 3.

Abstract

[reaction: see text] The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-catalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.

摘要

[反应:见正文] 报道了通过铱催化芳烃的硼化反应一锅法合成芳基硼酸和芳基三氟硼酸盐。为制备芳基硼酸,在铱催化的硼化反应之后,用高碘酸钠对硼酸酯进行氧化裂解。为制备芳基三氟硼酸盐,在铱催化的硼化反应之后,用二氟氢化钾取代频哪醇。这两个两步反应序列得到的产物比最初形成的频哪醇硼酸酯对后续化学反应更具反应活性。

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