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Catalytic borylation of methane
Smith, Kyle T.,Berritt, Simon,Gonzá,lez-Moreiras, Mariano,Ahn, Seihwan,Smith III, Milton R.,Baik, Mu-Hyun,Mindiola, Daniel J. American Association for the Advancement of Scienc 2016 Science Vol.351 No.6280
<P>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 degrees C and 3500-kilopascal pressure led to yields as high as similar to 52%, turnover numbers of 100, and improved chemoselectivity for monoborylated versus diborylated methane.</P>