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Regioselective Stepwise Synthesis of Unsymmetrical 1,2,5-Triarylpyrroles via Palladium-Catalyzed Decarboxylative Cross-Coupling and C-H Arylation

Author(s): Buonomano C; Patterson S; Ngou JS; Messina C; Taylor S; Bilodeau F; Forgione P;

Pyrrole derivatives are natural organic molecules that are important to the pharmaceutical industry due to their occurrence in nature and their use in a wide range of medical applications. In general, non-symmetric, 1,2,5-triaryl-substituted pyrroles are prepared either by Paal-Knorr condensation or cycloaddition that present synthetic challenges particul ...

Article GUID: 41900086


A Modular and Regioselective Synthesis of Di- and Triarylated Thiophenes: Strategies for Accessing Challenging Isomeric Motifs

Author(s): Messina C; McKibbon K; Wong KS; Prevost P; Petkov V; Forgione P;

This work demonstrates a highly modular, fully regioselective, and high-yielding route to accessing a variety of multiarylated thiophene motifs. Specifically, this method was used to generate unique diarylated (2,5 or 3,5 or 4,5), triarylated (2,3,5 or 2,4,5 or 3,4,5), and tetra-arylated (2,3,4,5) thiophenes, and branched oligothiophenes. Our approach ena ...

Article GUID: 41160050


Diverse Applications of Biomass-Derived 5-Hydroxymethylfurfural and Derivatives as Renewable Starting Materials

Author(s): Chacón-Huete F; Messina C; Cigana B; Forgione P;

This Review summarizes recent efforts to capitalize on 5-hydroxymethylfurfural (HMF) and related furans as emerging building blocks for the synthesis of fine chemicals and materials, with a focus on advanced applications within medicinal and polymer chemistry, as well as nanomaterials. As with all chemical industries, these fields have historically relied ...

Article GUID: 35652539


Programmed Synthesis of Tetra-Aryl Thiophenes with Stepwise, Ester-Controlled Regioselectivity

Author(s): Messina C; Ottenwaelder X; Forgione P;

Herein, we report a modular synthetic route to access tetra-arylated thiophene compounds with four different substituents with programmed chemical control provided by an ester activating/directing group. This method enables the functionalization of individual positions of thiophene sequentially via regioselective halogenations and cross-coupling reactions ...

Article GUID: 34506149


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