An Efficient Oxidation of Element-Containing Propargyl Alcohols and Acetylenic γ-Diols by 2-Iodoxybenzoic Acid (IBX)

Catalytic oxidation reactions often suffer from drawbacks such as low yields and poor selectivity. Particularly, selective oxidation of alcohols becomes more difficult when a compound contains more than one oxidizable functional group. In order to deliver a methodology that addresses these issues, herein we report an efficient, aerobic, chemoselective and simplified approach to oxidize a broad range of benzyl and propargyl alcohols containing diverse functional groups to their corresponding aldehydes and ketones in excellent yields under mild reaction conditions. Optimal yields were obtained at room temperature using 1 mmol substrate, 10 mol % copper(I) iodide, 10 mol % 4-dimethylaminopyridine (DMAP), and 1 mol % 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO) in acetonitrile, under an oxygen balloon. The catalytic system can be applied even when sensitive and oxidizable groups such as alkynes, amines, and phenols are present; starting materials and products containing such groups were found to be stable under the developed conditions.

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Conjugated Ynones in Organic Synthesis

Nájera

2019

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This review article will consider the preparation and application of ynones in synthetic organic chemistry. Concerning the preparation of these bifunctional compounds, several methodologies starting from propargyl alcohols, acyl derivatives, both by using alkynylmetal reagents or by transition metal (mainly palladium and copper) catalyzed alkynylations, carbon monoxide (carbonylation of terminal alkynes and alkenes), and other substrates will be discussed. The reactivity and synthetic applications of ynones will be focused on conjugate additions with boron-, carbon-, nitrogen-, oxygen-, and other heteroatom-containing nucleophiles, as well as radicals. Then, cycloaddition processes will include [2 + 2] cycloadditions, [3 + 2] 1,3-dipolar cycloadditions (with azides, nitrones, azomethine imines and ylides, nitrile oxides, diazo compounds, and other dipoles), and [4 + 2] cycloadditions (mainly Diels–Alder-type reactions). The reduction of the triple bond, addition to the carbonyl group (using carbon- and heteronucleophiles and reductions), and other not so commonly used processes (such as aldol reactions, cyclizations, and isomerizations) will be considered at the end.

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An Efficient Oxidation of Element-Containing Propargyl Alcohols and Acetylenic γ-Diols by 2-Iodoxybenzoic Acid (IBX)

Cited by 6 publications

References 22 publications

ChemInform Abstract: An Efficient Oxidation of Element‐Containing Propargyl Alcohols and Acetylenic γ‐Diols by 2‐Iodoxybenzoic Acid (IBX).

ChemInform Abstract: An Efficient Oxidation of Element‐Containing Propargyl Alcohols and Acetylenic γ‐Diols by 2‐Iodoxybenzoic Acid (IBX).

Chemoselective Oxidation of Benzyl, Amino, and Propargyl Alcohols to Aldehydes and Ketones under Mild Reaction Conditions

Conjugated Ynones in Organic Synthesis

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