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双金/银催化:通过串联C(sp)-H炔基化/亚氨基金化反应从2-取代吡啶衍生物合成中氮茚。

Dual Gold/Silver Catalysis: Indolizines from 2-Substituted Pyridine Derivatives via a Tandem C(sp)-H Alkynylation/Iminoauration.

作者信息

Han Chunyu, Liu Yaowen, Tian Xianhai, Rominger Frank, Hashmi A Stephen K

机构信息

Organisch Chemisches Institut, Heidelberg University, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia.

出版信息

Org Lett. 2021 Dec 17;23(24):9480-9484. doi: 10.1021/acs.orglett.1c03667. Epub 2021 Dec 7.

Abstract

A dual gold/silver-catalyzed cascade C(sp)-H alkynylation/iminoauration of 2-substituted pyridines with hypervalent iodine(III) reagents for the synthesis of indolizines is described. This novel reaction involves the formation of an alkynyl Au(III) species, a dual gold/silver-catalyzed C(sp)-H functionalization, and a subsequent iminoauration process. A number of indolizines bearing diverse functionalities were prepared in good to excellent yield. Furthermore, a gram-scale reaction was efficiently conducted.

摘要

描述了一种双金/银催化的2-取代吡啶与高价碘(III)试剂的级联C(sp)-H炔基化/亚氨基金化反应,用于合成中氮茚。这种新颖的反应涉及炔基金(III)物种的形成、双金/银催化的C(sp)-H官能化以及随后的亚氨基金化过程。制备了许多具有不同官能团的中氮茚,产率良好至优异。此外,还高效地进行了克级反应。

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