Nucleophilic borylation of fluorobenzenes with reduced arylboranes

• Published in: Chemical communications (Cambridge, England) Vol. 58; no. 2; pp. 254 - 257
• Main Authors: Budy, Hendrik, Prey, Sven E, Buch, Christoph D, Bolte, Michael, Lerner, Hans-Wolfram, Wagner, Matthias
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 23.12.2021; Royal Society of Chemistry
• Subjects: Boranes - chemistry; chemical communication; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Fluorobenzenes - chemistry; Lewis bases; Molecular Structure; Nucleophiles; Oxidation-Reduction; Physical Sciences; Science & Technology; synthesis; CHEMISTRY; ACTIVATION; VAN; BORON; BORANE; B(CN)(2-)
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d1cc06225e

Two challenging but rewarding topics in chemical synthesis are C-F-bond activation and the development of B-centered nucleophiles. We have now tackled both subjects simultaneously by forming aryl-B bonds via S N Ar-type reactions on fluorobenzenes under mild conditions using Na 2 [FluB&z.dbd;BFlu], Li 2 [HBFlu], and Li 2 [Me 2 DBA] (BFlu = 9-borafluorenyl, Me 2 DBA = 9,10-dimethyl-9,10-dihydro-9,10-diboraanthracene). Two challenging but rewarding topics in chemical synthesis are C-F-bond activation and development of B-centered nucleophiles. We have now tackled both subjects by forming aryl-B bonds via S N Ar-type reactions on fluorobenzenes under mild conditions.