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Straightforward formation of the unprecedented 5-membered annulated ring containing the B-N moiety: 1H-2,1-benzazaborolyl alkali metal salts, reactivity with electrophiles and redox behavior

Autoři: Hejda Martin | Jambor Roman | Růžička Aleš | Lyčka Antonín | Dostál Libor

Rok: 2015

Druh publikace: ostatní - přednáška nebo poster

Strana od-do: nestránkováno

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Jazyk	Název	Abstrakt	Klíčová slova
eng	Straightforward formation of the unprecedented 5-membered annulated ring containing the B-N moiety: 1H-2,1-benzazaborolyl alkali metal salts, reactivity with electrophiles and redox behavior	1,2-azaborolyl anion is known in the literature for a long time and already has been used as ligand for both transition and main group metals as cyclopentadienyl class ligand analogues. However, there are no reports dealing with analogous benzannulated 1H-2,1-benzazaboroles in this respect. Recently, we have found,[iii] that reduction of variously substituted C,N-chelated chloroboranes with potassium metal afforded various derivatives of symmetric (3,3’)-bis(1H-2,1-benzazaborole). Subsequent reduction of these compounds with two equivalents of alkali metal (M = Li, Na or K) proceeds via unique reaction pathway and produced the first 1H-2,1-benzazaborolyl (Bab) alkali metal salts M+(THF)(Bab)-. These salts are extremely strong reducing agents. Nevertherless, they are still able to react with simple electrophiles under formation of substituted 1H-2,1-benzazaboroles, but they also convert with starting C,N-chelated chloroboranes to unsymmetrically substituted (3,3’)-bis(1H-2,1-benzazaborole), thereby opening a new strategy for preparation of such C-C bridged heterocyclic systems. Reaction mechanisms, molecular structures, some experimental data and the latest results will be reported.

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