Ni~(II), Cu~(II) and Zn~(II) complexes with a sterically hindered scorpionate ligand (Tpms~(Ph)) and catalytic application in the diasteroselective nitroaldol (Henry) reaction

Bruno G. M. Rocha; Tatiana C. O. Mac Leod; M. Fátima C. Guedes da Silva; Konstantin V. Luzyanin; Luísa M. D. R. S. Martins; Armando J. L. Pombeiro

首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Ni~(II), Cu~(II) and Zn~(II) complexes with a sterically hindered scorpionate ligand (Tpms~(Ph)) and catalytic application in the diasteroselective nitroaldol (Henry) reaction

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Ni~(II), Cu~(II) and Zn~(II) complexes with a sterically hindered scorpionate ligand (Tpms~(Ph)) and catalytic application in the diasteroselective nitroaldol (Henry) reaction

机译：Ni〜（II），Cu〜（II）和Zn〜（II）与空间受阻的蝎子配体（Tpms〜（Ph））的配合物以及在非对映选择性硝基醛（Henry）反应中的催化应用

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The Ni~(II) and Zn~(II) complexes [MCl(Tpms~(Ph))] (Tpms~(Ph) = SO3C(pzPh)3, pz = pyrazolyl; M = Ni 2 or Zn 3) and the Cu~(II) complex [CuCl(Tpms~(Ph))(H2O)] (4) have been prepared by treatment of the lithium salt of the sterically demanding and coordination flexible tris(3-phenyl-1-pyrazolyl)methanesulfonate (Tpms~(Ph))~- (1) with the respective metal chlorides. The (Tpms~(Ph))~- ligand shows the N_3 or N_2O coordination modes in 2 and 3 or in 4, respectively. Upon reaction of 2 and 3 with Ag(CF_3SO_3) in acetonitrile the complexes [M(Tpms~(Ph))~- (MeCN)](CF_3SO_3) (M = Ni 5 or Zn 6, respectively) were formed. The compounds were obtained in good yields and characterized by analytic and spectral (IR, ~1H and ~(13)C{~1H} NMR, ESI-MS) data, density functional theory (DFT) methods and {for 4 and [~nBu_4N](Tpms~(Ph)) (7), the latter obtained upon Li~+ replacement by [~nBu_4N]~+ in Li(Tpms~(Ph))} by single crystal X-ray diffraction analysis. The Zn~(II) and Cu~(II) complexes (3 and 4, respectively) act as efficient catalyst precursors for the diastereoselective nitroaldol reaction of benzaldehydes and nitroethane to the corresponding β-nitroalkanols (up to 99% yield, at room temperature) with diastereoselectivity towards the formation of the anti isomer, whereas the Ni~(II) complex 2 only shows a modest catalytic activity.

机译：Ni〜（II）和Zn〜（II）配合物[MCl（Tpms〜（Ph））]（Tpms〜（Ph）= SO3C（pzPh）3，pz =吡唑基; M = Ni 2或Zn 3）和Cu（II）络合物[CuCl（Tpms〜（Ph））（H2O）]（4）是通过处理空间需求和配位的柔性三（3-苯基-1-吡唑基）甲磺酸盐的锂盐制备的（4） Tpms〜（Ph））〜-（1）与相应的金属氯化物。（Tpms〜（Ph））〜配体分别以2和3或4表示N_3或N_2O配位模式。 2和3与Ag（CF_3SO_3）在乙腈中反应后，形成配合物[M（Tpms〜（Ph））〜-（MeCN）]（CF_3SO_3）（分别为M = Ni 5或Zn 6）。以良好的收率获得了这些化合物，并通过分析和光谱（IR，〜1H和〜（13）C {〜1H} NMR，ESI-MS）数据，密度泛函理论（DFT）方法以及{对于4和[〜 nBu_4N]（Tpms〜（Ph））（7），通过单晶X射线衍射分析，将Li〜+替换为Li（Tpms〜（Ph））中的[〜nBu_4N]〜+。 Zn〜（II）和Cu〜（II）配合物（分别为3和4）可作为高效的催化剂前体，用于苯甲醛和硝基乙烷的非对映选择性硝基缩醛反应生成相应的β-硝基烷醇（在室温下收率高达99％））对反异构体的形成具有非对映选择性，而Ni〜（II）配合物2仅显示适度的催化活性。

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《Dalton transactions: An international journal of inorganic chemistry》 |2014年第40期|共9页
作者
Bruno G. M. Rocha; Tatiana C. O. Mac Leod; M. Fátima C. Guedes da Silva; Konstantin V. Luzyanin; Luísa M. D. R. S. Martins; Armando J. L. Pombeiro;
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complexes; sterically; catalytic;

机译：配合物;空间;催化;

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1. Ni~(II), Cu~(II) and Zn~(II) complexes with a sterically hindered scorpionate ligand (Tpms~(Ph)) and catalytic application in the diasteroselective nitroaldol (Henry) reaction [J] . Bruno G. M. Rocha, Tatiana C. O. Mac Leod, M. Fátima C. Guedes da Silva, Dalton transactions: An international journal of inorganic chemistry . 2014,第40期

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7. NiII, CuII and ZnII complexes with a sterically hindered scorpionate ligand (TpmsPh) and catalytic application in the diasteroselective nitroaldol (Henry) reaction [O] . Rocha Bruno G. M., MacLeod Tatiana C. O., Silva M. Fátima C. Guedes da, 2014

机译：NiII，CuII和ZnII与空间受阻的蝎子配体（TpmsPh）的配合物以及在非对映选择性硝基羟醛（Henry）反应中的催化应用

Ni~(II), Cu~(II) and Zn~(II) complexes with a sterically hindered scorpionate ligand (Tpms~(Ph)) and catalytic application in the diasteroselective nitroaldol (Henry) reaction

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