A New Pathway for the Synthesis of Ketones from Aldehydes and Sulfonylhydrazones: Is Diazo the Key Intermediate?

Author:

Wang Yue‐xing1,Chen Li‐ping1,Cao Feng‐de1,Zhao Bin1,Li Zhen‐peng1,Li Xiu‐fen1,Huang Long‐jiang12ORCID

Affiliation:

1. State Key Laboratory Base for Eco-Chemical Engineering College of Chemical Engineering Qingdao University of Science and Technology 266042 Qingdao Shandong P. R. China

2. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica Chinese Academy of Medical Sciences and Peking Union Medical College 100050 Beijing P. R. China

Abstract

AbstractA new pathway via a cyclic intermediate for the synthesis of ketones from aldehydes and sulfonylhydrazone derivatives under basic conditions is proposed. Several control experiments were performed along with analysis of the mass spectra and in‐situ IR spectra of the reaction mixture. Inspired by the new mechanism, an efficient and scalable method for homologation of aldehydes to ketones was developed. A wide variety of target ketones were obtained in yields of 42–95 % by simply heating the 3‐(trifluoromethyl)benzene sulfonylhydrazones (3‐(Tfsyl)hydrazone) for 2 h at 110 °C with aldehydes and with K2CO3 and DMSO as base and solvent, respectively.

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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