Details

Autor(en) / Beteiligte

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

Titel

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

Ist Teil von

• Journal of organic chemistry, 2015-06, Vol.80 (11), p.5771-5782

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2015

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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.