Development of a Novel Three‐step Sonogashira Cross Coupling/Deacetonation/Cycloaddition Protocol for the Synthesis of 4‐aryl‐1, 2, 3‐triazoles Using 2‐methyl‐3‐butyn‐2‐ol as a Versatile Acetylene Surrogate. Issue 5 (30th March 2021)

• Record Type: Journal Article
• Authors: da Silva, Everton M.; de Albuquerque, Danilo Yano; Zukerman‐Schpector, Julio; Schwab, Ricardo S.
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 5(2021)
• Page Start: 1153
• Page End: 1160
• Publication Date: 2021-03-30
• Subjects: MEBYNOL -- 1, 2, 3-triazoles -- Sustainable -- Three-step -- Deacetonation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100086
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A practical, and efficient microwave‐assisted, three‐step Sonogashira cross‐coupling/Deacetonation/Cycloaddition sequence has been developed for the synthesis of a variety of 4‐aryl‐1, 2, 3‐triazoles from readily available starting materials. The important features of this synthetic sequence include the use of inexpensive 2‐methyl‐3‐butyn‐2‐ol as an acetylene surrogate, 2‐Me‐THF as a bio‐based solvent, short reaction time, good yields, avoiding the isolation of volatile terminal alkynes. Abstract : This work presents a novel and simple route to synthesize 4‐aryl‐1, 2, 3‐triazole by the three‐step Sonogashira cross coupling/Deacetonation/Cycloaddition three‐step sequence under microwave irradiation. Furthermore, the protocol proceeds under mild conditions starting from 2‐methyl‐3‐butyn‐2‐ol as an acetylene surrogate in the presence of bio‐based solvent 2‐Me‐THF.