Publication

Pd(II)/PIDA‐Enabled Migratory Triple Functionalization of Terminal Alkenes via a 1,2‐C/Pd(IV) Dyotropic Rearrangement

2025

Abstract

We report a Pd(II)‐catalyzed migratory triple functionalization of terminal alkenes. The reaction of homoallylic amides with phenyliodine(III) diacetate (PIDA) under Pd(II) catalysis delivers 6‐acetoxylated 5,6‐dihydro‐4 H ‐1,3‐oxazines through the formation of one C─C and two C─O bonds. Mechanistic studies suggest a sequence involving oxypalladation, oxidation of Pd(II) to Pd(IV), a 1,2‐alkyl(aryl)/Pd(IV) dyotropic rearrangement (DR), and subsequent acetoxylation. While Pd(II)/Pd(IV) catalysis with PIDA as the oxidant has enabled numerous powerful transformations, the DR reported here is unprecedented.

Official source

https://infoscience.epfl.ch/entities/publication/e39d7c0f-e0c2-4652-ba9e-f69a8e16604d

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2025

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/e39d7c0f-e0c2-4652-ba9e-f69a8e16604d

About this result

Related concepts (10)

Alkene

In organic chemistry, an alkene is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or in the terminal position. Terminal alkenes are also known as α-olefins. The International Union of Pure and Applied Chemistry (IUPAC) recommends using the name "alkene" only for acyclic hydrocarbons with just one double bond; alkadiene, alkatriene, etc., or polyene for acyclic hydrocarbons with two or more double bonds; cycloalkene, cycloalkadiene, etc.

Alpha-olefin

In organic chemistry, alpha-olefins (or α-olefins) are a family of organic compounds which are alkenes (also known as olefins) with a chemical formula , distinguished by having a double bond at the primary or alpha (α) position. This location of a double bond enhances the reactivity of the compound and makes it useful for a number of applications. There are two types of alpha-olefins, branched and linear (or normal).

Alkyne

Acetylene Propyne 1-Butyne In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond. The simplest acyclic alkynes with only one triple bond and no other functional groups form a homologous series with the general chemical formula . Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to , known formally as ethyne using IUPAC nomenclature. Like other hydrocarbons, alkynes are generally hydrophobic.