Microwave‐Assisted Condensation of Benzylic Alcohols and Alkynes Promoted by Zinc Halides: Concise Access to Alkenyl Halides. Issue 34 (13th September 2021)

• Record Type: Journal Article
• Authors: Nandi, Poulomi; Goel, Komal; Sreenivasulu, Chinnabattigalla; Satyanarayana, Gedu
• Is Part Of: European journal of organic chemistry. Issue 34(2021)
• Page Start: 4851
• Page End: 4860
• Publication Date: 2021-09-13
• Subjects: Alkenyl halides -- Halogenation -- Lewis acids -- Microwave-assisted -- Terminal acetylenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100779
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A simple Lewis acid‐mediated route for the synthesis of alkenyl halides are described under microwave‐assisted conditions. The reaction proceeds through the condensation between secondary alcohols and terminal acetylenes and regioselective hydrohalogenation across the triple bond in the presence of simple and commercially available zinc halides. Unlike earlier reports, this methodology is successfully exemplified with three halide sources. As a result, a diverse range of alkenyl halide products has been accomplished. Further, indenes were obtained as the end products when tertiary alcohols and arylacetylenes were used, wherein the Thorpe–Ingold and electronic effects, would be dominant. Furthermore, when an electron‐rich arylacetylene was employed, the reaction directed to yield carbonyl products. Abstract : A simple Lewis acid‐mediated route for the synthesis of alkenyl halides are described under microwave‐assisted conditions. The reaction proceeds through the condensation between sec‐alcohols and terminal acetylenes and regeoselective hydro halogenation across the triple bond in the presence of simple and commercially available zinc halides. Three halide sources could successfully be employed to give a diverse range of alkenyl halide products as well as indenes and carbonyl products.