Publication

A Practical, One-Pot Multicomponent Synthesis of α-Amidosulfides and Their Application as Latent N-Acylimines in the Friedel-Crafts Reaction

2011
Journal Articles

Abstract

A novel one-pot, three-component synthesis of N-acyl or N-carbamoyl-alpha-amidosulfides 4 is described. The three-component reaction of aldehydes 1, primary carbamates (or amides) 2 and phenylsulfinic acid (6a) afforded alpha-amidosulfones 7, which after addition of sodium thiolate were in situ transformed into stable alpha-amidosulfides 4 in good to excellent yields. We demonstrated that silver salts or Bronsted acids were able to promote the formation of aliphatic and aromatic N-acylimines from 4 in quantitative yield under mild conditions. The phosphoric acid catalyzed Friedel-Crafts alkylation of 3-substituted indoles with alpha-amidosulfides 4 leading to 2,3-disubstitued indoles was also documented.

Official source

https://infoscience.epfl.ch/entities/publication/daee589a-1d9c-4679-9720-4e866d433646

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2011
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/daee589a-1d9c-4679-9720-4e866d433646

About this result

Related concepts (20)

Electrophilic aromatic substitution

Electrophilic aromatic substitution is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic nitration, aromatic halogenation, aromatic sulfonation, and alkylation and acylation Friedel–Crafts reaction. The most widely practised example of this reaction is the ethylation of benzene. Approximately 24,700,000 tons were produced in 1999.

Acid

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents.

Brønsted–Lowry acid–base theory

The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was first developed by Johannes Nicolaus Brønsted and Thomas Martin Lowry independently in 1923. The basic concept of this theory is that when an acid and a base react with each other, the acid forms its conjugate base, and the base forms its conjugate acid by exchange of a proton (the hydrogen cation, or H+). This theory generalises the Arrhenius theory.

Related publications (1)

A Practical, One-Pot Multicomponent Synthesis of α-Amidosulfides and Their Application as Latent N-Acylimines in the Friedel-Crafts Reaction

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