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Decennary Update on Oxidative-Rearrangement Involving 1,2-Aryl C-C Migration Around Alkenes: Synthetic and
1Department of Chemistry, MMEC, Maharishi Markandeshwar (Deemed to be University), Mullana, Ambala, 133207, Haryana (India.
Abstract:
In recent years, numerous methodologies on oxidative rearrangements of alkenes have been investigated, that produce multipurpose synthons and heterocyclic scaffolds of potential applications. The present review focused on recently established methodologies for oxidative transformation via 1,2-aryl migration in alkenes (2013-2023). Special emphasis has been placed on mechanistic pathways to understand the reactivity pattern of different substrates, challenges to enhance selectivity, the key role of different reagents, and effect of different substituents, and how they affect the rearrangement process. Moreover, synthetic limitations and future direction also have been discussed. We believe, this review offers new synthetic and mechanistic insight to develop elegant precursors and approaches to explore the utilization of alkene-based compounds for natural product synthesis and functional materials.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.