Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY.

Chem Commun (Camb)

State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Advanced Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210046, P. R. China.

Published: February 2021

AI Article Synopsis

  • Researchers developed a new series of benzo[a]-fused BODIPYs and naphthyl-BODIPYs through a one-pot chemical reaction using palladium as a catalyst.
  • The reaction involves a domino process where BODIPY precursors react with diarylethynes to form specific isomers based on the geometry of the addition (cis, cis vs. trans, cis).
  • This method shows a unique preference for cyclizing at the a-position of the BODIPY structure, allowing for controlled product formation by changing the substituents on the diarylethynes.

Article Abstract

A series of benzo[a]-fused BODIPYs and the corresponding isomeric naphthyl-BODIPYs have been synthesized through a facile one-pot palladium-catalyzed domino reaction of BODIPY precursors (2-bromo-BODIPYs) with diarylethynes, via "cis, cis" and "trans, cis" addition transition states with alkynes, respectively. This reaction exhibits unprecedentedly complete cyclization regioselectivity to the a-position of the BODIPY over the b-one, and the resulting products can be effectively regulated by the substituent choice on the diarylethynes.

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Source
http://dx.doi.org/10.1039/d0cc08163aDOI Listing

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