Pd-catalyzed copper-free carbonylative Sonogashira reaction of aryl iodides with alkynes for the synthesis of alkynyl ketones and flavones by using water as a solvent

Bo Liang; Mengwei Huang; Zejin You; Zhengchang Xiong; Kui Lu; Reza Fathi; Jiahua Chen; Zhen Yang

doi:10.1021/jo050498t

Pd-catalyzed copper-free carbonylative Sonogashira reaction of aryl iodides with alkynes for the synthesis of alkynyl ketones and flavones by using water as a solvent

J Org Chem. 2005 Jul 22;70(15):6097-100. doi: 10.1021/jo050498t.

Authors

Bo Liang¹, Mengwei Huang, Zejin You, Zhengchang Xiong, Kui Lu, Reza Fathi, Jiahua Chen, Zhen Yang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education, College of Chemistry, School of Pharmaceutical Science, ShenZhen Graduate School, Peking University, Beijing 100871, China.

PMID: 16018709
DOI: 10.1021/jo050498t

Abstract

The Pd-catalyzed copper-free carbonylative Sonogashira coupling reaction to synthesize alkynyl ketones from terminal alkynes and aryl iodides was achieved by using water as a solvent. The reaction was carried out at room temperature under balloon pressure of CO with Et(3)N as a base. The developed method was successfully applied to the synthesis of flavones.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Copper / chemistry
Cyclization
Flavones / chemical synthesis*
Hydrocarbons, Aromatic / chemistry
Hydrocarbons, Iodinated / chemistry*
Ketones / chemical synthesis*
Molecular Structure
Palladium / chemistry*
Water / chemistry

Substances

Alkynes
Flavones
Hydrocarbons, Aromatic
Hydrocarbons, Iodinated
Ketones
Water
Palladium
Copper