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Scope and Limitations of the Liebeskind–Srogl Cross-Coupling Reactions Involving the Biellmann BODIPY

2015; American Chemical Society; Volume: 80; Issue: 11 Linguagem: Inglês

10.1021/acs.joc.5b00731

1520-6904

Lourdes Betancourt-Mendiola, Ismael Valois‐Escamilla, Teresa Arbeloa, Jorge Bañuelos, Íñigo López‐Arbeloa, Juan O. Flores-Rizo, Rongrong Hu, Erik Lager, César F. A. Gómez‐Durán, José L. Belmonte‐Vázquez, Mayra R. Martínez-González, Ismael J. Arroyo‐Córdoba, Carlos A. Osorio-Martı́nez, Enrique Alvarado‐Martínez, Arlette Urías‐Benavides, Brenda D. Gutiérrez‐Ramos, Ben Zhong Tang, Eduardo Peña‐Cabrera,

Porphyrin and Phthalocyanine Chemistry

Several new examples of meso-(het)arylBODIPY were prepared via the Liebeskind-Srogl (L-S) cross-coupling reaction of the Biellmann BODIPYs (1a,b) and aryl- and heteroarylboronic acids in good to excellent yield. It was shown that this reaction could be carried out under microwave heating to shorten reaction times and/or increase the yield. It was illustrated that organostannanes also participate in the L-S reaction to give the corresponding BODIPY analogues in short reaction times and also with good to excellent yields. We analyze the role of the substituent at the sensitive meso position in the photophysical signatures of these compounds. In particular, the rotational motion of the aryl ring and the electron donor ability of the anchored moieties rule the nonradiative pathways and, hence, have a deep impact in the fluorescence efficiency.