Microwave‐Assisted Condensation of Benzylic Alcohols and Alkynes Promoted by Zinc Halides: Concise Access to Alkenyl Halides

Nandi, Poulomi and Goel, Komal and Sreenivasulu, Chinnabattigalla and Satyanarayana, G. (2021) Microwave‐Assisted Condensation of Benzylic Alcohols and Alkynes Promoted by Zinc Halides: Concise Access to Alkenyl Halides. European Journal of Organic Chemistry, 2021 (34). pp. 4851-4860. ISSN 1434-193X

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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. © 2021 Wiley-VCH GmbH

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IITH Creators:

IITH Creators	ORCiD
Satyanarayana, G.	UNSPECIFIED

Item Type:

Article

Additional Information:

We are grateful to the Department of Science and Technology Science and Engineering Research Board (DST‐SERB) [No. EMR/2017/005312], New Delhi, for financial support. K. G & C. B. S thank UGC for the award of the research fellowship.

Uncontrolled Keywords:

Alkenyl halides; Halogenation; Lewis acids; Microwave-assisted; Terminal acetylenes

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

08 Sep 2022 13:40

Last Modified:

08 Sep 2022 13:40