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

Authors: Messina CMcKibbon KWong KSPrevost PPetkov VForgione P


Affiliations

1 Concordia University, 7141 Sherbrooke St W, Montréal, Québec H4B 1R6, Canada.
2 Centre in Green Chemistry and Catalysis, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, Québec H2V 0B3, Canada.
3 Centre for NanoScience Research, 7141 Sherbrooke St W, Montréal, Québec H4B 1R6, Canada.

Description

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 enables independent introduction of each arene, providing full control over the desired molecular structure. Given that 2,5-aryl-substituted thiophenes are highly sought-after and that aryl substitution at the 3 and 4 positions was previously highly challenging to obtain, our approach represents a facile means to generate these attractive molecules for the next generation of thiophene-based technologies.


Links

PubMed: https://pubmed.ncbi.nlm.nih.gov/41160050/

DOI: 10.1021/acs.joc.5c01700