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Issue 33, 2014
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From C,N- and N,N-chelated chloroboranes to substituted 1H-2,1-benzazaboroles and 1H-pyrrolo[1,2-c][1,3,2]diazaborolidines: a straightforward route to five-membered rings containing the B–N or N–B–N moiety

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Abstract

A set of 1H-2,1-benzazaboroles as B–N analogues of 1H-indene and a set of 1H-pyrrolo[1,2-c][1,3,2]diazaborolidines as B–N analogues of 1H-pyrrolizine were prepared via nucleophilic addition of selected alkyl(aryl)lithiums (MeLi, tBuLi or PhLi) to, via N→B intramolecular interactions, the activated imino C[double bond, length as m-dash]N functionality in the structure of C,N- or N,N-chelated chloroboranes. All compounds were characterized by elemental analysis and 1H, 11B, 13C and 15N NMR spectroscopy, and molecular structures of isolated compounds were on several occasions established by means of single-crystal X-ray diffraction analysis. The presence of three adjacently bonded substituents and their systematic alternation on five-membered C3BN (1H-2,1-benzazaboroles) or C2BN2 (1H-pyrrolo[1,2-c][1,3,2]diazaborolidines) rings allowed us to follow both the influence of the steric repulsion and limitations for the formation of respective annulated heterocyclic systems.

Graphical abstract: From C,N- and N,N-chelated chloroboranes to substituted 1H-2,1-benzazaboroles and 1H-pyrrolo[1,2-c][1,3,2]diazaborolidines: a straightforward route to five-membered rings containing the B–N or N–B–N moiety

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Publication details

The article was received on 16 May 2014, accepted on 20 Jun 2014 and first published on 23 Jun 2014


Article type: Paper
DOI: 10.1039/C4DT01445F
Citation: Dalton Trans., 2014,43, 12678-12688
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    From C,N- and N,N-chelated chloroboranes to substituted 1H-2,1-benzazaboroles and 1H-pyrrolo[1,2-c][1,3,2]diazaborolidines: a straightforward route to five-membered rings containing the B–N or N–B–N moiety

    M. Hejda, A. Lyčka, R. Jambor, A. Růžička and L. Dostál, Dalton Trans., 2014, 43, 12678
    DOI: 10.1039/C4DT01445F

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