5-Aminopyrazole-4-carbonitrile and ethyl 5-aminopyrazole-4-carboxylate, as potential trifunctional building blocks are introduced in a facile, chemo- and regioselective multicomponent assembly of imidazo[1,2-b]pyrazoles via the Groebke-Blackburn-Bienaymé reaction (GBB reaction). Besides the synthetic elaboration of a green-compatible isocyanide-based access in three-component mode, we describe ...

A transition-metal-free carboxyamidation process, using aryl diazonium tetrafluoroborates and isocyanides under mild conditions, has been developed. This novel conversion was initiated by a base and solvent induced aryl radical, followed by radical addition to isocyanide and single electron transfer (SET) oxidation, affording the corresponding arylcarboxyamide upon hydration of the nitrilium in...

A new reaction model, tandem Michael addition/formal isocyanide insertion into the acyl C-C bond, has been developed. Thus, a series of 2-acylpyrroles and seven-/eight-membered ring fused pyrroles were synthesized from the reaction of methyl isocyanides with enones in a single operation.

A sequential one-pot approach towards N,N'-disubstituted guanidines from N-chlorophthalimide, isocyanides and amines is reported. This strategy provides straightforward and efficient access to diverse guanidines in yields up to 81% through previously unprecedented N-phthaloylguanidines. This protocol also features wide substrate scope and mild conditions.

Efficient access to a large chemical space based on new scaffolds with defined 3D conformations and highly variable in the side chains is needed to find novel functional materials. Four heterocyclic scaffolds based on a four component Ugi reaction of α-amino acids, oxo components, isocyanides and primary or secondary amines suitably functionalized are described. A handful of examples are descri...

The m-terphenyl isocyanides CNAr(Mes2) and CNAr(Dipp2) support five-coordinate, isocyanide/carbonyl monoanions of manganese. For CNAr(Dipp2), a bis-isocyanide anion is available that is remarkably well behaved upon reaction with electrophiles. Most notable is the formation of an unprecedented chloride-substituted metallostannylene.

The radical fluoroalkylation of isocyanides with fluorinated sulfones is enabled by visible-light photoredox catalysis. A wide range of readily available mono-, di-, and trifluoromethyl heteroaryl sulfones can thus be used as efficient radical fluoroalkylation reagents under mild conditions. This method not only describes a new synthetic application of fluorinated sulfones, but also provides a ...

The reaction between a transition metal carbonyl compound, L(n)MCO, and Li[Me(3)SiNR] yields the corresponding isocyanide derivative, L(n)MCNR, thereby providing a new route to transition metal isocyanide compounds that does not require the use of free isocyanides as reagents.

An efficient route to 5H-benzo[d]imidazo[5,1-b][1,3]thiazines has been developed using the copper(i)-catalyzed tandem reaction of o-alkynylphenyl isothiocyanates with isocyanides in THF with Cs2CO3 as base. The present tandem process allows the assembly of a variety of 5H-benzo[d]imidazo[5,1-b][1,3]thiazines in good to excellent yields.