Transition Metal‐free Phosphorylation of Vinyl Azides: A Convenient Synthesis of β‐Ketophosphine Oxides

Jang, Ji-Hoon; Kim, Dae Young

doi:10.1002/bkcs.11964

Cited by 12 publications

(2 citation statements)

References 68 publications

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“…A broad array of 3-acylspiro [4,5]-trienone scaffolds was synthesized by Tang's group through a photocatalytic tandem reaction of N-(p-methoxyaryl)propiolamides with acyl chlorides (Scheme 22a) [86]. This reaction features a broad scope with high selectivity.…”

Section: Scheme 18 (A) Acylarylation Reaction Of Aromatic Carboxylic Acids and Methacrylamides; (B) Acyl Radical-mediated Difunctionalizamentioning

confidence: 99%

“…Carbonyl-containing compounds, such as ketones, esters and amides, widely exist in numerous biologically important natural products, functional materials as well as pharmaceuticals [1][2][3][4][5]. The development of efficient methods toward synthesis of these substantial compounds has been intensively pursued by synthetic chemists over the past decades.…”

Section: Introductionmentioning

confidence: 99%

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Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Liu

Xiao

2020

Catalysts

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Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors.

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Section: Scheme 18 (A) Acylarylation Reaction Of Aromatic Carboxylic Acids and Methacrylamides; (B) Acyl Radical-mediated Difunctionalizamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Liu

Xiao

2020

Catalysts

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Electrochemical Oxidative Selenolactonization of Alkenoic Acids with Diselenides: Synthesis of Selenated γ‐Lactones

2021

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Electrochemical N‐Centered Radical Addition/Semipinacol Rearrangement Sequence of Alkenyl Cyclobutanols: Synthesis of β‐Amino Cyclic Ketones

Jang

Kim

2022

Asian J Org Chem

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The electrochemical N-centered radical addition/ semipinacol rearrangement sequence of alkenyl cyclobutanols with sulfonimides is described. This transformation is an environmentally friendly approach that uses cheap and easily handled sulfonimides as N-centered radical sources and successfully avoiding the use of stoichiometric amounts of external redox reagents. The β-amino cyclic ketone derivatives could be synthesized in moderate to high yields from alkenyl cyclobutanol derivatives under mild constant current electrolysis conditions.

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Transition Metal‐free Phosphorylation of Vinyl Azides: A Convenient Synthesis of β‐Ketophosphine Oxides

Abstract: A convenient synthesis of β‐ketophosphine oxides using vinyl azides.

Cited by 12 publications

References 68 publications

Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Electrochemical Oxidative Selenolactonization of Alkenoic Acids with Diselenides: Synthesis of Selenated γ‐Lactones

Electrochemical N‐Centered Radical Addition/Semipinacol Rearrangement Sequence of Alkenyl Cyclobutanols: Synthesis of β‐Amino Cyclic Ketones

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