Catalyst-controlled selectivity in the C-H borylation of methane and ethane

Amanda K. Cook, Sydonie D. Schimler, Adam J. Matzger, Melanie S. Sanford

Research output: Contribution to journalArticlepeer-review

161 Scopus citations


The C-H bonds of methane are generally more kinetically inert than those of other hydrocarbons, reaction solvents, and methane functionalization products.Thus, developing strategies to achieve selective functionalization of CH4 remains a major challenge. Here, we report transitionmetal-catalyzed C-Hborylation ofmethane with bis-pinacolborane (B2pin2) in cyclohexane solvent at 150°C under 2800 to 3500 kilopascals of methane pressure. Iridium, rhodium, and ruthenium complexes all catalyze the reaction. Formation of mono- versus diborylatedmethane is tunable as a function of catalyst, with the ruthenium complex providing the highest ratio of CH3Bpin to CH2(Bpin)2. Despite the high relative concentration of cyclohexane, minimal quantities of borylated cyclohexane products are observed. Furthermore, all three metal complexes catalyze borylation of methane with >3.5:1 selectivity over ethane.

Original languageEnglish (US)
Pages (from-to)1421-1424
Number of pages4
Issue number6280
StatePublished - Mar 25 2016
Externally publishedYes


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