Hydroamination of alkenes with dinitrogen and titanium polyhydrides

Takanori Shima (), Qingde Zhuo, Xiaoxi Zhou, Ping Wu, Ryota Owada, Gen Luo () and Zhaomin Hou ()
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Takanori Shima: RIKEN Center for Sustainable Resource Science
Qingde Zhuo: RIKEN Cluster for Pioneering Research
Xiaoxi Zhou: RIKEN Cluster for Pioneering Research
Ping Wu: Anhui University
Ryota Owada: RIKEN Cluster for Pioneering Research
Gen Luo: Anhui University
Zhaomin Hou: RIKEN Center for Sustainable Resource Science

Nature, 2024, vol. 632, issue 8024, 307-312

Abstract: Abstract An ideal synthesis of alkyl amines would involve the direct use of abundant and easily accessible molecules such as dinitrogen (N2) and feedstock alkenes1–4. However, this ambition remains a great challenge as it is usually difficult to simultaneously activate both N2 and a simple alkene and combine them together through carbon–nitrogen (C–N) bond formation. Currently, the synthesis of alkyl amines relies on the use of ammonia produced through the Haber–Bosch process and prefunctionalized electrophilic carbon sources. Here we report the hydroamination of simple alkenes with N2 in a trititanium hydride framework, which activates both alkenes and N2, leading to selective C–N bond formation and providing the corresponding alkyl amines on further hydrogenation and protonation. Computational studies reveal key mechanistic details of N2 activation and selective C–N bond formation. This work demonstrates a strategy for the transformation of N2 and simple hydrocarbons into nitrogen-containing organic compounds mediated by a multinuclear hydride framework.

Date: 2024
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DOI: 10.1038/s41586-024-07694-5

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