Our group recently discovered the first base metal catalysts for C-H borylation by using metal-metal cooperativity as a design strategy. Using heterobimetallic catalysts with polar Cu-Fe and Zn-Fe bonds, a variety of arene substrates were borylated under photochemical conditions. One of the main practical limitations of the new technology was the requirement for UV irradiation. On the basis of mechanistic experiments, approaches towards shifting from photochemical activation to thermal activation of the catalysts will be discussed in this contribution. Substrate scope and regioselectivity considerations also will be examined. The ultimate goal of mimicking the C-H borylation chemistry of precious metal catalysts with base metal substitutes has potential ramifications on the cost and price stability of large-scale applications in synthesis.

Toward practical C-H borylation with base metal catalysts

247th National Meeting (2014)

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