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. 2011 Aug 22;50(35):8157-60.
doi: 10.1002/anie.201103192. Epub 2011 Jul 12.

Nucleophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborine

Ashley N Lamm  1 , Edward B Garner 3rd, David A Dixon, Shih-Yuan Liu
Affiliations

Nucleophilic aromatic substitution reactions of 1,2-dihydro-1,2-azaborine

Ashley N Lamm et al. Angew Chem Int Ed Engl. .

Abstract

Could go either way: the addition of nucleophiles to the parent 1,2-dihydro-1,2-azaborine and subsequent quenching with an electrophile generates novel substituted 1,2-azaborine derivatives. Mechanistic studies are consistent with two distinct nucleophilic aromatic substitution pathways depending on the nature of the nucleophile.

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Figures

Figure 1
Figure 1
Calculated free energies in Et2O (G3MP2 + COSMO solvation model at the B3LYP-DZVP2 level) of the proposed intermediates in the SNAr reaction at 298 K.
Scheme 1
Scheme 1
Possible reaction pathways of the substitution reaction.
See this image and copyright information in PMC

References

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    1. Liu Z, Marder TB. Angew. Chem. Int. Ed. 2008;47:242–244. - PubMed

    1. For fundamental and synthetic contributions, see: Tanjaroon C, Daly A, Marwitz AJV, Liu S-Y, Kukolich S. J. Chem. Phys. 2009;131 224312. Daly AM, Tanjaroon C, Marwitz AJV, Liu S-Y, Kukolich SG. J. Am. Chem. Soc. 2010;132:5501–5506. Marwitz AJV, Abbey ER, Jenkins JT, Zakharov LN, Liu SY. Org. Lett. 2007;9:4905–4908. Marwitz AJV, McClintock SP, Zakharov LN, Liu SY. Chem. Commun. 2010;46:779–781. Lamm AN, Liu SY. Mol. BioSyst. 2009;5:1303–1305.

    1. For work related to materials science, see: Marwitz AJV, Jenkins JT, Zakharov LN, Liu S-Y. Angew. Chem. Int. Ed. 2010;49:7444–7447.

    1. For potential biomedical applications, see: Abbey ER, Zakharov LN, Liu S-Y. J. Am. Chem. Soc. 2010;132:16340–16342. Liu L, Marwitz AJV, Matthews BW, Liu S-Y. Angew. Chem. Int. Ed. 2009;48:6817–6819.

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