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. 2011 Dec 21;133(50):20152-5.
doi: 10.1021/ja2097089. Epub 2011 Nov 21.

A 1,3-dihydro-1,3-azaborine debuts

Senmiao Xu  1 , Lev N Zakharov, Shih-Yuan Liu
Affiliations

A 1,3-dihydro-1,3-azaborine debuts

Senmiao Xu et al. J Am Chem Soc. .

Abstract

We present the first synthesis and characterization of a 1,3-dihydro-1,3-azaborine, a long-sought BN isostere of benzene. 1,3-Dihydro-1,3-azaborine is a stable structural motif with considerable aromatic character as evidenced by structural analysis and its reaction chemistry. Single crystal X-ray analysis indicates bonding consistent with significant electron delocalization. 1,3-Dihydro-1,3-azaborines also undergo nucleophilic substitutions at boron and electrophilic aromatic substitution reactions. In view of the versatility and impact of aromatic compounds in the biomedical field and in materials science, the present study further expands the available chemical space of arenes via BN/CC isosterism.

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Figures

Figure 1
Figure 1
ORTEP illustrations, with thermal ellipsoids drawn at the 35% probability level, of compound 4.
Scheme 1
Scheme 1
The Three BN Isosteres of Benzene
Scheme 2
Scheme 2
Retrosynthetic Analysis
Scheme 3
Scheme 3
Synthesis of Precursor 9
Scheme 4
Scheme 4
Synthesis and Characterization of Piano Stool Complex 11
See this image and copyright information in PMC

References

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