Journal ArticleDOI
Metal-catalyzed electrochemical diazidation of alkenes
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TLDR
An operationally simple and environmentally friendly protocol that converts alkenes and sodium azide—both readily available feedstocks—to 1,2-diazides and can be smoothly reduced to vicinal diamines in a single step, with high chemoselectivity.Abstract:
Vicinal diamines are a common structural motif in bioactive natural products, therapeutic agents, and molecular catalysts, motivating the continuing development of efficient, selective, and sustainable technologies for their preparation. We report an operationally simple and environmentally friendly protocol that converts alkenes and sodium azide—both readily available feedstocks—to 1,2-diazides. Powered by electricity and catalyzed by Earth-abundant manganese, this transformation proceeds under mild conditions and exhibits exceptional substrate generality and functional group compatibility. Using standard protocols, the resultant 1,2-diazides can be smoothly reduced to vicinal diamines in a single step, with high chemoselectivity. Mechanistic studies are consistent with metal-mediated azidyl radical transfer as the predominant pathway, enabling dual carbon-nitrogen bond formation.read more
Citations
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References
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Click Chemistry: Diverse Chemical Function from a Few Good Reactions.
TL;DR: In this paper, a set of powerful, highly reliable, and selective reactions for the rapid synthesis of useful new compounds and combinatorial libraries through heteroatom links (C-X-C), an approach called click chemistry is defined, enabled, and constrained by a handful of nearly perfect "springloaded" reactions.
Journal ArticleDOI
Catalytic Asymmetric Dihydroxylation
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Solar Synthesis: Prospects in Visible Light Photocatalysis
TL;DR: A variety of reaction types have now been shown to be amenable to visible light photocatalysis via photoinduced electron transfer to or from the transition metal chromophore, as well as energy-transfer processes.
Journal ArticleDOI
Organic Azides: An Exploding Diversity of a Unique Class of Compounds
TL;DR: In this Review, the fundamental characteristics of azide chemistry and current developments are presented and the focus will be placed on cycloadditions (Huisgen reaction), aza ylide chemistry, and the synthesis of heterocycles.
Journal ArticleDOI
Redox catalysis in organic electrosynthesis: basic principles and recent developments.
Robert Francke,R. Daniel Little +1 more
TL;DR: Progress is described in the field of electroorganic synthesis, a process that can be accomplished more efficiently and purposefully using modern computational tools, and summarizes recent advances.
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