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首页> 外文期刊>Catalysis science & technology >5,5 '-Bistriazoles as axially chiral, multidentate ligands: synthesis, configurational stability and catalytic application of their scandium(III) complexes
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5,5 '-Bistriazoles as axially chiral, multidentate ligands: synthesis, configurational stability and catalytic application of their scandium(III) complexes

机译：5、5 ' -Bistriazoles轴手性、多齿的配体:合成、构型和稳定钪的催化应用(3)复合物

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摘要

The design and development of 5,5'-bistriazoles featuring aminomethyl substituents is discussed. An efficient synthetic procedure for the selective preparation of 4,4'-bis.aminomethyl)-5,5'-bistriazoles from commercially available propargylamine derivatives and benzyl azide has been optimized. The first experimental determination of the configurational stability of 5,5'-bistriazoles is disclosed on the basis of rotational energy barriers and half-life times. Fast racemization was observed for a bistriazole possessing solely axial chirality whereas a more heavily substituted bistriazole involving axial and central chirality proved to be configurationally stable. A successful catalytic application has been implemented by using a N, Ndimethylpropargylamine- derived 5,5'-bistriazole as a multidentate ligand controlling the product selectivity (single vs. double addition) in scandium.III)-catalyzed nucleophilic additions of indoles to isatin electrophiles.
机译：设计和开发的5 ' -bistriazoles以氨甲基取代基进行了探讨。一个有效的合成过程选择性的制备4, 4’-bis.aminomethyl) 5、5 ' -bistriazoles商用propargylamine衍生品和苄基叠氮化进行了优化。实验测定的构型稳定的5 ' -bistriazoles披露转动能量壁垒和的基础半衰期时间。bistriazole拥有单纯轴向手性而更多地取代bistriazole涉及手性轴向和中部被证明是稳定的构型上。成功的催化应用实现通过使用N,Ndimethylpropargylamine - derived’-bistriazole 5.5%作为一个多齿的配体控制产品选择性(单引号和双之外)scandium.III)催化亲核的添加indoles to isatin electrophiles。

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