The nucleophilic addition of widely available and variously functionalized organolithium reagents to isothiocyanates represents a straightforward, high-yielding, one-pot method to access secondary thioamides. The simple reaction conditions required and the broad scope (>50 cases examples) makes it a robust and reliable method to access both simple and complex thioamides, including enantiopure ones. Noxious and unpleasant-smelling sulfurating agents, usually employed in the literature established methods, are avoided during the whole synthetic procedure thus, rendering the protocol highly attractive, also for sustainability aspects.

A Robust, Eco-Friendly Access to Secondary Thioamides through the Addition of Organolithium Reagents to Isothiocyanates in Cyclopentyl Methyl Ether (CPME) / V. Pace, L. Castoldi, S. Monticelli, S. Safranek, A. Roller, T. Langer, W. Holzer. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 21:52(2015 Oct 28), pp. 18966-18970. [10.1002/chem.201504247]

A Robust, Eco-Friendly Access to Secondary Thioamides through the Addition of Organolithium Reagents to Isothiocyanates in Cyclopentyl Methyl Ether (CPME)

L. Castoldi
Secondo
;
2015

Abstract

The nucleophilic addition of widely available and variously functionalized organolithium reagents to isothiocyanates represents a straightforward, high-yielding, one-pot method to access secondary thioamides. The simple reaction conditions required and the broad scope (>50 cases examples) makes it a robust and reliable method to access both simple and complex thioamides, including enantiopure ones. Noxious and unpleasant-smelling sulfurating agents, usually employed in the literature established methods, are avoided during the whole synthetic procedure thus, rendering the protocol highly attractive, also for sustainability aspects.
isothiocyanates; lithiation; nucleophilic addition; one-pot synthesis; thioamides
Settore CHIM/06 - Chimica Organica
Article (author)
File in questo prodotto:
File Dimensione Formato  
Chemistry A European J - 2015 - Pace - A Robust Eco%u2010Friendly Access to Secondary Thioamides through the Addition of.pdf

accesso riservato

Tipologia: Publisher's version/PDF
Dimensione 1.12 MB
Formato Adobe PDF
1.12 MB Adobe PDF   Visualizza/Apri   Richiedi una copia
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/890704
Citazioni
  • ???jsp.display-item.citation.pmc??? 4
  • Scopus 39
  • ???jsp.display-item.citation.isi??? 39
social impact