Catalytic borylation of methane

• Autores: Kyle T. Smith, Simon Berritt, Mariano González-Moreiras, Seihwan Ahn
• Localización: Science, ISSN 0036-8075, Vol. 351, Nº 6280, 2016, págs. 1424-1427
• Idioma: inglés
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• Resumen

  • Despite steady progress in catalytic methods for the borylation of hydrocarbons, methane has not yet been subject to this transformation. Here we report the iridium-catalyzed borylation of methane using bis(pinacolborane) in cyclohexane solvent. Initially, trace amounts of borylated products were detected with phenanthroline-coordinated Ir complexes. A combination of experimental high-pressure and high-throughput screening, and computational mechanism discovery techniques helped to rationalize the foundation of the catalysis and identify improved phosphine-coordinated catalytic complexes. Optimized conditions of 150°C and 3500-kilopascal pressure led to yields as high as ~52%, turnover numbers of 100, and improved chemoselectivity for monoborylated versus diborylated methane.