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Highly selective hydroaminomethylation of internal alkenes to give linear amines

机译：内部烯烃的高度选择性加氢氨基甲基化，生成线性胺

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摘要

The application of phenoxaphosphino-modified Xantphos-type ligands (1-9) in the rhodium-catalyzed hydroaminomethylation of internal olefins to give linear amines is reported. Excellent chemo- and regioselectivities have been obtained through the use of 0.1 mol% [Rh(cod)(2)]BF4/0.4 mol% xantphenoxaphos (1), providing a practical and environmentally attractive synthetic route for the preparation of amines from internal alkenes. For the first time, both functionalized internal olefins and mixtures of internal and terminal olefins have been converted highly selectively into linear amines. Investigations of the effects of the calculated natural bite angles of ligands on hydroaminomethylation shows that the regioselectivity for the linear product follows a similar trend to that seen in the hydroformylation of internal alkenes with the aid of these ligands. Hydroaminomethylation and each of its individual steps were monitored by high-pressure infrared spectroscopy. The results suggest that hydroaminomethylations take place by a sequential isomerization/hydroformylation/amination/hydrogenation pathway.
机译：据报道，苯氧磷膦改性的黄磷型配体（1-9）在铑催化的内烯烃加氢氨基甲基化反应中得到线性胺。通过使用0.1摩尔％[Rh（cod）（2）] BF4 / 0.4摩尔％黄嘌呤草磷（1）获得了出色的化学和区域选择性，为从内部烯烃制备胺提供了实用且对环境有吸引力的合成途径。第一次，官能化的内烯烃以及内烯烃和末端烯烃的混合物都被高度选择性地转化为线性胺。对所计算的配体的自然咬合角对氢氨基甲基化的影响的研究表明，线性产物的区域选择性遵循与借助这些配体的内部烯烃的氢甲酰化所观察到的趋势相似的趋势。通过高压红外光谱法监测氢氨基甲基化及其各个步骤。结果表明，氢氨基甲基化通过顺序异构化/加氢甲酰化/胺化/加氢途径发生。

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