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铑(III)催化二茂铁的 C-H 炔基化与高价碘试剂。

Rhodium(III)-Catalyzed C-H Alkynylation of Ferrocenes with Hypervalent Iodine Reagents.

机构信息

School of Physical Science and Technology, ShanghaiTech University , 100 Haike Road, Shanghai 201210, China.

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 LinglingLu, Shanghai 200032, China.

出版信息

J Org Chem. 2017 Nov 17;82(22):11829-11835. doi: 10.1021/acs.joc.7b00775. Epub 2017 May 9.

Abstract

Rapid access to mono- or dialkynylation of ferrocene with ethynylbenziodoxolones as the alkynylation reagents was achieved via rhodium-catalyzed direct C-H bond functionalization at room temperature. Mono- and dialkynylation were easily modulated by varying the sterical volume of the directing group, such as pyridine and isoquinoline, and amount of hypervalent iodine reagents. A wide range of ferrocene-based alkynylation products could be obtained in up to 94% yield, and a gram-scale reaction also proceeded smoothly with high efficiency.

摘要

通过室温下铑催化的直接 C-H 键官能化反应,乙炔基苯并[d]噁唑酮作为炔烃试剂可快速实现二茂铁的单炔基或二炔基化。通过改变导向基团(如吡啶和异喹啉)和高价碘试剂的用量,很容易调节单炔基和二炔基化反应。可以高达 94%的收率得到各种基于二茂铁的炔基化产物,克级反应也能以高收率顺利进行。

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