In:
Angewandte Chemie International Edition, Wiley, Vol. 55, No. 45 ( 2016-11-02), p. 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.
Type of Medium:
Online Resource
ISSN:
1433-7851
,
1521-3773
DOI:
10.1002/anie.201608520
Language:
English
Publisher:
Wiley
Publication Date:
2016
detail.hit.zdb_id:
2011836-3
detail.hit.zdb_id:
123227-7
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