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

Senmiao Xu; Lev N. Zakharov; Shih Yuan Liu

doi:10.1021/ja2097089

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

Senmiao Xu
, Lev N. Zakharov
, Shih Yuan Liu^*

^*Corresponding author for this work

University of Oregon

Research output: Contribution to journal › Article › peer-review

82 Scopus citations

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.

Original language	English
Pages (from-to)	20152-20155
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	50
DOIs	https://doi.org/10.1021/ja2097089
State	Published - 21 Dec 2011
Externally published	Yes

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10.1021/ja2097089

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title = "A 1,3-dihydro-1,3-azaborine debuts",

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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year = "2011",

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doi = "10.1021/ja2097089",

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AU - Xu, Senmiao

AU - Zakharov, Lev N.

AU - Liu, Shih Yuan

PY - 2011/12/21

Y1 - 2011/12/21

N2 - 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.

AB - 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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M3 - 文章

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 50

ER -

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

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