Electrophilic halogenations of propargyl alcohols: paths to α-haloenones, β-haloenones and mixed β,β-dihaloenones
Issued Date
2022-08-12
Resource Type
eISSN
20462069
Scopus ID
2-s2.0-85137547585
Journal Title
RSC Advances
Volume
12
Issue
35
Start Page
22678
End Page
22694
Rights Holder(s)
SCOPUS
Bibliographic Citation
RSC Advances Vol.12 No.35 (2022) , 22678-22694
Suggested Citation
Bovonsombat P., Sophanpanichkul P., Losuwanakul S. Electrophilic halogenations of propargyl alcohols: paths to α-haloenones, β-haloenones and mixed β,β-dihaloenones. RSC Advances Vol.12 No.35 (2022) , 22678-22694. 22694. doi:10.1039/d2ra03540e Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/87503
Title
Electrophilic halogenations of propargyl alcohols: paths to α-haloenones, β-haloenones and mixed β,β-dihaloenones
Author(s)
Author's Affiliation
Other Contributor(s)
Abstract
The Meyer-Schuster rearrangement of propargyl alcohols or alkynols leading to α,β-unsaturated carbonyl compounds is well known. Yet, electrophilic halogenations of the same alkynols and their alkoxy, ester and halo derivatives are inconspicuous. This review on the halogenation reactions of propargyl alcohols and derivatives intends to give a perspective from its humble direct halogenation beginning to the present involving metal catalysis. The halogenation products of propargyl alcohols include α-fluoroenones, α-chloroenones, α-bromoenones and α-iodoenones, as well as β-haloenones and symmetrical and mixed β,β-dihaloenones. They are, in essence, tri and tetrasubstituted alkenes carrying halo-functionalization at the α- or β-carbon. This is a potential stepping stone for further construction towards challenging substituted alkenones via Pd-catalysed coupling reactions.