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钴(CO)作为固体 CO(g)源,用于高度失活的(杂)芳基胺与(杂)芳基卤化物的氨基羰基化反应。

Co(CO) as a Solid CO (g) Source for the Amino Carbonylation of (Hetero)aryl Halides with Highly Deactivated (Hetero)arylamines.

机构信息

Department of Studies in Chemistry, Yuvaraja's College, University of Mysore, Mysuru, Karnataka 570005, India.

Ortin laboratories Pvt., Ltd., Malkapur Village, Choutuppal Mandal, Hyderabad, Telangana 508252, India.

出版信息

J Org Chem. 2021 Apr 16;86(8):5530-5537. doi: 10.1021/acs.joc.0c02999. Epub 2021 Apr 7.

Abstract

Carbonylation of (hetero)aryl iodides/bromides with highly deactivated 2-aminopyridines using Pd-Co(CO) bimetallic catalysis is accomplished. The use of Co(CO) as a solid CO(g) source enhanced reaction rates observed when compared to CO(g), and excellent yields highlight the versatility of the developed protocol. A wide range of electronically and sterically demanding heterocyclic amines and (hetero)aryl iodides/bromides employed for this study resulted in excellent yields of amino carbonylated products. The developed methodology was further extended to synthesize and luciferase inhibitors.

摘要

使用 Pd-Co(CO)双金属催化,实现了高度失活的 2-氨基吡啶与(杂)芳基碘化物/溴化物的羰基化反应。与 CO(g)相比,使用 Co(CO)作为固态 CO(g)源可以提高反应速率,并且优异的产率突出了所开发方案的多功能性。该研究中使用了广泛的电子和空间位阻要求高的杂环胺和(杂)芳基碘化物/溴化物,得到了氨基羰基化产物的优异产率。所开发的方法学进一步扩展到合成 和荧光素酶抑制剂。

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