Atom-Efficient Synthesis of Alkynylfluoroborates Using BF3 -Based Frustrated Lewis Pairs

Autor:	Konstantin Chernichenko, Vladimir Iashin, Imre Pápai, Timo Repo
Rok vydání:	2016
Předmět:	Steric effects Tetrafluoroborate 010405 organic chemistry General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry Borylation 01 natural sciences Catalysis Coupling reaction Frustrated Lewis pair 0104 chemical sciences chemistry.chemical_compound chemistry Organic chemistry Organic synthesis Lewis acids and bases Boron trifluoride
Zdroj:	Angewandte Chemie. 128:14352-14356
ISSN:	0044-8249
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::520f64c6de34c7ba3edb10d4a68d0a38 https://doi.org/10.1002/ange.201608520 Zobrazit plný text záznamu Plný text ve formátu PDF Plný text ve formátu HTML
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