Electrochemically Facilitated Interaction of O‐Nucleophiles with Imine Group in Electroactive ortho‐((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers,ChemistrySelect

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Electrochemically Facilitated Interaction of O‐Nucleophiles with Imine Group in Electroactive ortho‐((Ferrocenylimino)methyl)phenylboronate and Comparison with Its Regioisomers
ChemistrySelect ( IF 1.9 ) Pub Date : 2018-09-05 , DOI: 10.1002/slct.201802030
Martin Konhefr ₁ , Karel Lacina ₂ , Monika Skrutková Langmajerová ₁ , Zdeněk Glatz ₁ , Petr Skládal _{1,

2} , Ctibor Mazal _{2,

3}

Affiliation

Mutual position of imine and boronic acid moieties in ortho regioisomer of ((ferrocenylimino)methyl)phenylboronic acid (1 a) facilitates and highly favours reversible molecular switching between C=N imine and COR‐NH hemiaminal group. These two states are controllable electrochemically by oxidation/reduction of ferrocenyl moiety and thus a simple dynamic molecular switch for addition/elimination of nucleophile to/from the imine is formed. The exceptional redox behaviour of 1 a in protic primary alcohols is caused by the interaction of both the motif of the boronic acid moiety and imine carbon atom with the alcohol molecule. Thus, the behaviour of acids 1 is influenced by the type of solvent, oxidation state of the ferrocenyl residue and proximity of the boronic acid moiety. Moreover, other multiple equilibria covering majority of possible interactions of imine group and boronic acid moiety with surroundings including influence of various O‐nucleophiles have been addressed and described in detail within the interest in understanding the fundamental factors governing the B–N interaction.

中文翻译：

O-亲核试剂与亚胺基在电活性邻-（（二茂铁亚氨基）甲基）苯基硼酸酯中的电化学促进相互作用及其区域异构体的比较

亚胺和硼酸部分在（（二茂铁亚氨基）甲基）苯基硼酸（1 a）的邻域异构体中的相互位置有利于并非常有利于C = N亚胺和COR-NH半胱氨酸基团之间的可逆分子转换。这两个状态可通过二茂铁基部分的氧化/还原在电化学上控制，因此形成用于向/从亚胺添加/消除亲核试剂的简单动态分子开关。质子伯醇中1 a的特殊氧化还原行为是由于硼酸部分的基序和亚胺碳原子与醇分子的相互作用而引起的。因此，酸的行为1受溶剂的类型，二茂铁基残基的氧化态和硼酸部分的接近度的影响。此外，在了解理解支配B–N相互作用的基本因素的兴趣范围内，已解决并详细描述了涵盖亚胺基团和硼酸部分与周围环境（包括各种O-亲核试剂的影响）的大多数可能相互作用的其他多重平衡。

更新日期：2018-09-05

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