Abstract
AbstractA sterically demanding amine, 1,2,2,6,6‐pentamethylpiperidine (PMP), forms a highly reactive Lewis acid–base pair with boron trifluoride. This pair reacts with terminal acetylenes to give the products of C(sp)−H borylation, previously unknown tri‐ and tetraalkynylboron compounds. Trialkynylfluoroborates can serve as surrogates of alkynyltrifluoroborates for C−C coupling reactions. Using aqueous NaOH, PMP can be recovered from its tetrafluoroborate salt, which is formed as a C−H borylation byproduct. Combining the discovered borylation reactivity with the PMP recovery provides a straightforward and atom‐efficient approach to synthetically useful alkynylfluoroborates.
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