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Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations
2022-06-23 22:09

南方科技大学舒伟团队报道了用催化剂调节的区域聚合氢烷基化反应正交制备α-/β-支链/直链脂肪胺。相关研究成果发表在2022年6月21日出版的《德国应用化学》。

直链、α-支链和β-支链脂肪胺广泛存在于医药、农药和精细化学品中。因此,以可调谐的方式开发直接和高效的方法来处理这些结构是非常可取的,但也是具有挑战性的。

该文中,研究人员开发了由镍/共催化烯基胺与卤代烷的区域和位置选择性氢烷基化反应合成α-支链、β-支链和直链脂肪族胺的催化剂控制合成。该催化方案的特点是可靠预测和控制烷基化的偶联位置,以提供从相同起始材料获得α-支链、β-支链和直链烷基胺的正交途径。该平台解锁了氢化镍和氢化钴化学的正交反应性和选择性,以在温和条件下催化三种烷基胺的再利用。

线性、α-支链和β-支链脂肪胺广泛存在于医药、农药和精细化工领域。因此,发展直接和有效的方法,以一种可调的方式,这些结构是非常可取的,但具有挑战性。

附:英文原文

Title: Orthogonal Access to α-/β-Branched/Linear Aliphatic Amines by Catalyst-Tuned Regiodivergent Hydroalkylations

Author: Peng-Fei Yang, Wei Shu

Issue&Volume: 2022-06-21

Abstract: Linear, α-branched, and β-branched aliphatic amines are widespread in pharmaceuticals, agrochemicals, and fine chemicals. Thus, the development of direct and efficient methods to these structures in a tunable manner is highly desirable yet challenging. Herein, a catalyst-controlled synthesis of α-branched, β-branched and linear aliphatic amines from Ni/Co-catalyzed regio- and site-selective hydroalkylations of alkenyl amines with alkyl halides is developed. This catalytic protocol features the reliable prediction and control of the coupling position of alkylation to provide orthogonal access to α-branched, β-branched and linear alkyl amines from identical starting materials. This platform unlocks orthogonal reactivity and selectivity of nickel hydride and cobalt hydride chemistry to catalytically repurpose three types of alkyl amines under mild conditions.

DOI: 10.1002/anie.202208018

Source: https://onlinelibrary.wiley.com/doi/10.1002/anie.202208018

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