A Robust, Eco-Friendly Access to Secondary Thioamides through the Addition of Organolithium Reagents to Isothiocyanates in Cyclopentyl Methyl Ether (CPME).
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.
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 1090, Vienna (Austria). vittorio.pace@univie.ac.at.
Vittorio
V
Pace
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 1090, Vienna (Austria).
Laura
L
Castoldi
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 1090, Vienna (Austria).
Serena
S
Monticelli
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 1090, Vienna (Austria).
Sandra
S
Safranek
Institute of Inorganic Chemistry, University of Vienna, Währingerstrasse 42 1090, Vienna (Austria).
Alexander
A
Roller
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 1090, Vienna (Austria).
Thierry
T
Langer
Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14 1090, Vienna (Austria).
Wolfgang
W
Holzer
isothiocyanates; lithiation; nucleophilic addition; one-pot synthesis; thioamides