The Suzuki-Miyaura cross-coupling reaction is one of the more powerful methods available for the formation of new carbon-carbon bonds, and potassium organotrifluoroborates have recently proven useful as alternative reagents in such reactions because of their increased stability to air and moisture and reduced protodeboronation. Additionally, unprecedented reagents and reactivities are possible with this class of reagents.Aminomethyl moieties are critical substructures in many important contexts. Currently, limitations exist for the incorporation of this subunit into organic molecules. Potassium Boc-protected aminomethyltrifluoroborates have been investigated and proven to be good coupling partners in Suzuki coupling reactions with aryl- and heteroaryl halides and pseudohalides, providing a very important, complementary means to access diverse aminomethylated arenes.

Synthesis and Suzuki–Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborates

244th National Meeting (2012)

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