Site-Selective, Catalyst-Controlled Alkene Aziridination

Site-Selective, Catalyst-Controlled Alkene Aziridination
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位点选择性、催化剂控制的烯烃氮丙啶化

DOI:
10.1055/s-0037-1609858
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发表时间:
2018
期刊:
Synthesis
影响因子:
--
通讯作者:
Schomaker, Jennifer
Schomaker, Jennifer
中科院分区:
--
文献类型:
--
作者:
Mat Lani, Amirah;Schomaker, Jennifer

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过渡金属催化氮烯转移反应是一种简便的方法,可以通过烯烃氮丙啶化或C-H键胺化将氮引入简单的底物中。银配合物具有不寻常的能力,以适应广泛的N-供体配体和协调的氮烯转移催化剂的几何结构。这种行为导致能够实现氮丙啶化和C-H键酰胺化之间的可调化学选择性,以及两个不同C-H键之间的可调位点选择性官能化。在本文中,努力从事银和铑催化剂的多样性,以实现选择性和可调的烯烃混合物的氮杂环丙烷化进行了讨论。有人发现,双核铑催化剂的选择性主要取决于空间效应,而银上的配体的身份可以调整,以影响是否在竞争烯烃的空间或电子功能是控制哪种前体优先氮丙啶化的主要因素。
Transition-metal-catalyzed nitrene transfer is a convenient method to introduce nitrogen into simple substrates through either alkene aziridination or C–H bond amination. Silver complexes have an unusual capability to accommodate a broad range of N-donor ligands and coordination geometries in catalysts competent for nitrene transfer. This behavior has resulted in the ability to achieve tunable chemoselectivity between aziridination and C–H bond amidation, as well as tunable site-selective functionalization between two different C–H bonds. In this paper, efforts to engage the diversity of silver and rhodium catalysts to accomplish selective and tunable aziridination of mixtures of alkenes are discussed. It was found that the selectivity of dinuclear Rh catalysts is dictated largely by steric effects, while the identity of the ligand on silver can be tuned to influence whether the steric or electronic features in the competing alkenes is the primary factor controlling which precursor is preferentially aziridinated.
DOI: 10.1021/ol303167n
发表时间: 2013-01-18
期刊: ORGANIC LETTERS
影响因子: 5.2
作者:
Rigoli, Jared W.;Weatherly, Cale D.;Vo, Brian T.;Neale, Samuel;Meis, Alan R.;Schomaker, Jennifer M.
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发表时间: 1971
影响因子: 2.3
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发表时间: 2014-09-02
期刊: TETRAHEDRON
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