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通过 Ir 催化的 C-H 硼化/N-C(O)活化实现酰胺的高选择性和发散性酰基和芳基交叉偶联。

Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation.

机构信息

Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States.

出版信息

Org Lett. 2020 Aug 7;22(15):6010-6015. doi: 10.1021/acs.orglett.0c02105. Epub 2020 Jul 9.

Abstract

Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C-H borylation/N-C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C-H borylation and divergent acyl and decarbonylative amide N-C(O) and C-C activation. The methodology diverts the traditional acylation and arylation regioselectivity, allowing us to directly utilize readily available arenes and amides to produce valuable ketone and biaryl motifs.

摘要

在此,我们证明酰胺可以通过顺序的 Ir 催化 C-H 硼化/N-C(O)活化与非活化芳环轻易偶联。这种方法通过空间控制的 Ir 催化 C-H 硼化和发散的酰基和脱羰酰胺 N-C(O)和 C-C 活化,为二芳基酮和二芳基的合成提供了简便的途径。该方法改变了传统的酰化和芳基化区域选择性,使我们能够直接利用易得的芳环和酰胺来生产有价值的酮和二芳基基序。

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