Synthesis of B/Ga and B/In Heteronuclear Bidentate Lewis Acids: Formation of Intramolecular pi-Arene-Gallium(III) and -Indium(III) Complexes

Marcus Schulte; Francois P.Gabbai

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Synthesis of B/Ga and B/In Heteronuclear Bidentate Lewis Acids: Formation of Intramolecular pi-Arene-Gallium(III) and -Indium(III) Complexes

机译：B / Ga和B / In异核双齿路易斯酸的合成：分子内π-芳烃-镓（III）和-铟（III）配合物的形成

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Reaction of 1,8-dilithionaphthalene·TMEDA (TMEDA = tetramethylethylenediamine) with dimesitylbor-on fluoridein diethyl ether followed by treatment with THF affords the Li(THF)_4 salt of dimesityl-1,8-naphthalenediylborate (1). Compound 1-Li(THF)_4 undergoes a ring-opening reaction with trimethyltin chloride to afford high yields of 1-(dimetylboron)-8-(trimethyltin)naphthalenediyl (2), a compound in which a boryl and a stannyl moiety coexist at the peri positions of a naphthalene core. Compound 2 has been characterized by multinuclear NMR spectroscopy, elemental analysis, and X-ray single-crystal analysis which reveal the existence of a sterically crowded structure. Compound 2 is a useful starting material for the synthesis of other heteronuclear naphthalene derivatives. Thus, the transmetalation reaction of 2 with GaCl_3 or InCl_3 in THF results in high yields of 1-(dichlorogallium)-8-(dimethysitylboron)-naphthlalenediyl (4), respectively. These unprecedented boron/gallium and boron/indium heteronuclear bidentate Lewis acids have been characterized by multinuclear NMR spectroscopy, elemental analysis, and X-ray single-crystal analyis. Owing to the presence of a short contact between the ipso-carbon atom of a mesityl group and the heavy Group 13 element (C_ipso-Ga 2.279(4)A for 3, C_ipso-In 2.442(6)A for 4), compounds 3 and 4 are best described as intramolecular pi-arene complexes and are the first examples of such complexes,. As shown by ~1H and ~13C NMR spectroscopy, this pi interaction subsists in solution.

机译：使1,8-二锂基萘·TMEDA（TMEDA =四甲基乙二胺）与二氟苯乙烯上的氟化二氟乙醚反应，然后用THF处理，得到二芳基-1,8-萘二甲硼酸酯的Li（THF）_4盐（1）。化合物1-Li（THF）_4与三甲基氯化锡进行开环反应，以提供高产率的1-（二甲基硼）-8-（三甲基锡）萘二甲酰基（2），该化合物中的硼烷基和苯乙烯基部分共存于萘核的周边位置。化合物2已通过多核NMR光谱，元素分析和X射线单晶分析进行了表征，揭示了空间拥挤结构的存在。化合物2是用于合成其他杂核萘衍生物的有用的起始原料。因此，2与GaCl_3或InCl_3在THF中的金属转移反应分别导致高产率的1-（二氯镓）-8-（二甲基苯乙烯基）-萘二烯基（4）。这些空前的硼/镓和硼/铟杂核双齿路易斯酸已经通过多核NMR光谱，元素分析和X射线单晶分析进行了表征。由于异丁基的ipso-碳原子与13族重元素（C_ipso-Ga 2.279（4）A为3，C_ipso-In 2.442（6）A为4）之间存在短接触，因此化合物3 1和4最好被描述为分子内pi-芳烃配合物，并且是此类配合物的第一个实例。如〜1H和〜13C NMR光谱所示，此pi相互作用存在于溶液中。

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《Chemistry: A European journal》 |2002年第16期|共6页
作者
Marcus Schulte; Francois P.Gabbai;
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正文语种 eng
中图分类化学;应用化学;
关键词
boron; gallium; indium; lewis acids; pi interactions;

机译：硼;镓;铟;路易斯酸;pi相互作用;

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1. Synthesis of B/Ga and B/In Heteronuclear Bidentate Lewis Acids: Formation of Intramolecular pi-Arene-Gallium(III) and -Indium(III) Complexes [J] . Marcus Schulte, Francois P.Gabbai Chemistry: A European journal . 2002,第16期

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Synthesis of B/Ga and B/In Heteronuclear Bidentate Lewis Acids: Formation of Intramolecular pi-Arene-Gallium(III) and -Indium(III) Complexes

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