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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Reactivity of C,N-chelated organoboron compounds with lithium anilides-formation of unexpected 1,2,3-trisubstituted 1H-2,1-benzazaboroles
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Reactivity of C,N-chelated organoboron compounds with lithium anilides-formation of unexpected 1,2,3-trisubstituted 1H-2,1-benzazaboroles

机译：C，N螯合的有机硼化合物与苯甲酸锂的反应性-形成意外的1,2,3-三取代的1H-2,1-苯并氮杂硼烷

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摘要

A set of C,N-intramolecularly coordinated boranes containing various C,N-chelating ligands L~(1-3) (where L~1 = [o-(CHNtBu)C _6H_4], L~2 = [o-(CHN-2,6-iPr_2C _6H_3)C_6H_4], L~3 = [o-(CH_2NMe_2)C_6H_4]); L ~(1-3)BCl_2 (for 1 L = L~1, for 2 L = L~2, for 5 L = L~3), L~1BPhCl (3) and L~1BCy _2 (4) (where Cy = cyclohexyl) were synthesized and fully characterized by multinuclear NMR spectroscopy and in cases of 1 and 3-5 by the single crystal X-ray diffraction analysis. The reaction of 1-3 with the anilides ArNHLi (Ar = 2,6-Me_2C_6H_3 or 2,6-iPr _2C_6H_3) proceeded via unexpected addition of anilide across the CN bond yielding 1,2,3-trisubstituted 1H-2,1-benzazaboroles 6-11, whose structures were unambiguously established by single crystal X-ray diffraction analysis (except for 11) and multinuclear NMR spectroscopy. In contrast, compounds 4 and 5 were inert towards ArNHLi. The investigation dealing with the reaction mechanism between the parent boranes 1-3 and ArNHLi revealed that amidolithiation of the CN double bond involved in the ligand backbones is the crucial step of the whole reaction. The CN double bond in 1-3 is activated by its coordination to the ortho bonded Lewis acidic boron center, which was also proven by the fact that the non-substituted ligand L~1H did not react with ArNHLi under the same reaction conditions in an analogous reaction.
机译：一组含有各种C，N螯合配体L〜（1-3）的C，N分子内配位的硼烷（其中L〜1 = [o-（CHNtBu）C _6H_4]，L〜2 = [o-（CHN -2,6-iPr_2C _6H_3）C_6H_4]，L〜3 = [o-（CH_2NMe_2）C_6H_4]）; L〜（1-3）BCl_2（对于1 L = L〜1，对于2 L = L〜2，对于5 L = L〜3），L〜1BPhCl（3）和L〜1BCy _2（4）（其中（Cy =环己基）合成并通过多核NMR光谱进行全面表征，在1和3-5情况下通过单晶X射线衍射分析进行表征。 1-3与苯甲酸酯ArNHLi（Ar = 2,6-Me_2C_6H_3或2,6-iPr _2C_6H_3）的反应是通过在CN键上意外地添加苯胺来进行的，得到1,2,3-三取代的1H-2,1-苯并氮杂硼烷6-11，其结构通过单晶X射线衍射分析（11除外）和多核NMR光谱确定。相反，化合物4和5对ArNHLi是惰性的。有关母体硼烷1-3与ArNHLi之间反应机理的研究表明，参与配体主链的CN双键的酰胺基化是整个反应的关键步骤。 1-3中的CN双键通过与邻键的Lewis酸性硼中心的配位而被激活，这也得到以下事实的证明：在相同的反应条件下，未取代的配体L〜1H在相同的反应条件下不会与ArNHLi反应类似的反应。

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