Atom‐Efficient Synthesis of Alkynylfluoroborates Using BF3‐Based Frustrated Lewis Pairs
- 6 October 2016
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition
- Vol. 55 (45) , 14146-14150
Abstract
A 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.Keywords
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