An Expeditious Approach to α, α‐Dihalo‐α′‐acetoxyketones from Propargylic Acetates. Issue 27 (22nd September 2017)

• Record Type: Journal Article
• Authors: Sadhukhan, Santu; Baire, Beeraiah
• Is Part Of: ChemistrySelect. Volume 2:Issue 27(2017)
• Page Start: 8500
• Page End: 8503
• Publication Date: 2017-09-22
• Subjects: alkynes -- dihaloketones -- hydration reaction -- metal free strategy -- propargylic acetates; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201701398
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A Regioselective and efficient synthesis of α, α‐diiodo‐α′‐acetoxyketones as well as α, α‐dibromo‐α′ ‐acetoxyketones has been achieved from the propargylic acetates and N ‐iodo(bromo)succinimides in the absence of any added promoters. This transformation is very general and shown compatibility for all structural types of propargylic acetates with terminal alkyne unit, such as tertiary ‐ (aryl‐aryl; aryl‐alkyl; alkyl‐alkyl), secondary‐ (aryl; alkyl), primary‐; and hence provided access to structurally divergent and highly important halogenated building blocks. Abstract : Highly regioselective and efficient synthesis of α, α‐dihalo‐α′‐acetoxyketones has been achieved from the propargylic acetates and N ‐iodo(bromo)succinimides in the absence of any added promoters.