Radical-based functionalization-oriented construction: rapid assembly of azaarene-substituted highly functionalized pyrroles

Abstract

Totally different functionalization and construction as two fundamental synthetic protocols have long been applied to furnish azaarene variants. Here, a novel radical-based functionalization-oriented construction strategy by exploiting the electronic properties...

Asymmetric Photocatalytic Synthesis of Enantioenriched Azaarene Derivatives

“…It is also highly desired to realize the enantioselective fashion towards the newly developed functionalization-oriented construction, a useful strategy to assemble more than two azaarene motifs into the molecular architectures. [41] In addition, to provide more kinds of valuable enantiomerically pure azaarene variants to serve on the advance of pharmaceutical and material industry, new and other viable asymmetric catalysis platforms require to explore. Notably, the exploitation of the unmet enamine-containing azaarene-triggering reactions, wherein the aromaticity of azaarenes is maintained, still remains an attractive task.…”

Visible Light‐Mediated Manipulation of 1,n‐Enynes in Organic Synthesis

“…[39] In this context, the DPZ photoredox catalysed synthesis of functionalized pyrroles 35 from N-aryl α-amino acids 33 and 2-azaarene bearing 1,3enynes 34 was recently established by Jiang, Cao, and coworkers (Scheme 12). [40] The important step of this reaction was the generation of nucleophilic α-aminyl radical 12 A from the respective amino acids 33, which then reacts with the 1,3-…”

“…In this context, the DPZ photoredox catalysed synthesis of functionalized pyrroles 35 from N ‐aryl α‐amino acids 33 and 2‐azaarene bearing 1,3‐enynes 34 was recently established by Jiang, Cao, and co‐workers (Scheme 12). [40] The important step of this reaction was the generation of nucleophilic α‐aminyl radical 12 A from the respective amino acids 33 , which then reacts with the 1,3‐enynes 34 , eventually leading to the cyclized product 35 . The authors employed DPZ as a photocatalyst with NaH 2 PO 4 as an additive under visible light irradiation.…”

Flexible Construction Approach to the Synthesis of 1,5-Substituted Pyrrole-3-carbaldehydes from 5-Bromo-1,2,3-triazine

“…Most of the approaches rely on intramolecular heteroannulation for ring closure via C–N bond formation. The substrates bearing both amino and alkyne groups in these reactions are either prepared or formed in situ . To prevent the production of complex byproducts, these reactions frequently employ 2-nitro and 2-trifluoromethyl 1,3-enynes as designed substrates in cascade intermolecular cyclization with amines to form the corresponding pyrrole derivatives. − However, the preparation of these substrates usually requires a tedious multistep synthesis, and these methods are not suitable for the synthesis of substituted pyrrole-3-carbaldehydes.…”