A facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl3 as the CO source

Guanglong Sun; Min Lei; Lihong Hu

doi:10.1039/C6RA02424F

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A facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl₃ as the CO source†

Guanglong Sun,^a Min Lei*^a and Lihong Hu*^a

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* Corresponding authors

^a State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai, P. R. China
E-mail: mlei@simm.ac.cn, lhhu@simm.ac.cn

Abstract

A facile and efficient method for the synthesis of alkynones by a Pd-catalyzed carbonylative Sonogashira coupling reaction starting from aryl iodide, terminal alkyne and chloroform (CHCl₃) as the CO source is described. This procedure proves that CHCl₃ is a cheap and efficient CO source in the presence of CsOH·H₂O as the base. Furthermore, it is applied successfully for the modification of natural products, such as vindoline and tabersonin, to obtain the corresponding products in good yields.

This article is part of the themed collection: Editors’ collection: Catalytic Organic Transformations

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Article information

DOI: https://doi.org/10.1039/C6RA02424F
Article type: Communication
Submitted: 27 Jan 2016
Accepted: 11 Mar 2016
First published: 15 Mar 2016

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RSC Adv., 2016,6, 28442-28446

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A facile and efficient method for the synthesis of alkynone by carbonylative Sonogashira coupling using CHCl₃ as the CO source

G. Sun, M. Lei and L. Hu, RSC Adv., 2016, 6, 28442 DOI: 10.1039/C6RA02424F

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