Gold(III)-catalyzed synthesis of 2, 5-disubstituted furans from substituted 5-methoxyhex-3-yn-2-ols—Mechanistic outlook. Issue 20 (18th October 2021)

• Record Type: Journal Article
• Authors: Behera, Sagarika; Bera, Nabakumar; Sarkar, Debayan
• Is Part Of: Synthetic communications. Volume 51:Issue 20(2021)
• Page Start: 3090
• Page End: 3098
• Publication Date: 2021-10-18
• Subjects: Allenyl carbocation -- 5-endo-dig -- one-pot -- open-air -- propargyl ether; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2021.1961274
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Gold(III)-catalyzed activation of alkynes has been applied for the synthesis of 2, 5-disubstituted furans from substituted 5-methoxy-hex-3-yn-2-ols. Mechanistically, the reaction proceeds via an allenyl carbocation intermediate followed by 5-endo-dig cyclization. The high-yielding, open-air, room temperature reaction conditions applied to synthesize a series of alkyl, aryl, and hetero aryl-substituted furans provide uniqueness to the strategy. Graphical Abstract: UF0001