Journal ArticleDOI
N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes
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TLDR
It is found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce ary lkyl ketones.Abstract:
We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon–carbon bond is proposed.read more
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The Persistent Radical Effect in Organic Synthesis
TL;DR: Although great progress has been achieved over the years in enantioselective radical chemistry, the radical-metal crossover approach offers advantages, in particular considering the non-existing background coupling leading to racemic compounds.
Journal ArticleDOI
Recent advances in the chemistry and applications of N-heterocyclic carbenes
TL;DR: In this article, a review of N-heterocyclic carbenes encompassing their history, properties and applications in transition metal catalysis, on-surface chemistry, main group chemistry and organocatalysis is provided.
Journal ArticleDOI
N-Heterocyclic Carbene-Based Catalysis Enabling Cross-Coupling Reactions
Hirohisa Ohmiya,Hirohisa Ohmiya +1 more
TL;DR: The use of N-Heterocyclic carbene (NHC) organocatalysis to promote umpolung reactions has emerged as a powerful tool for modern organic synthesis as discussed by the authors.
Journal ArticleDOI
Recent advances in N-heterocyclic carbene-based radical catalysis
TL;DR: This minireview highlights the recent progress and developments in NHC-based radical catalysis and is categorized according to the reaction types; oxidation type reaction and carbon–carbon bond formation through single electron transfer/radical–radical coupling.
Journal ArticleDOI
N-Heterocyclic Carbene-Catalyzed Radical Relay Enabling Vicinal Alkylacylation of Alkenes.
TL;DR: This protocol introduces tertiary alkyl groups and acyl groups to C-C double bonds with complete regioselectivity to produce functionalized ketone derivatives.
References
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An overview of N-heterocyclic carbenes
TL;DR: A concise overview of N-heterocyclic carbenes in modern chemistry is provided, summarizing their general properties and uses and highlighting how these features are being exploited in a selection of pioneering recent studies.
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Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.
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Photosensitized decarboxylative Michael addition through N-(acyloxy)phthalimides via an electron-transfer mechanism
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Biomimetic Carbene‐Catalyzed Oxidations of Aldehydes Using TEMPO
TL;DR: 2,2,6,6-tetramethylpiperidine N-oxyl radical (TEMPO), which has been used successfully by the group in transition-metal-mediated reactions and in various radical processes, is used as the oxidant to oxidize enamines of type C by organic single-electron transfer (SET) oxidants.
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N-Heterocyclic Carbene Catalysis via the α,β-Unsaturated Acyl Azolium
TL;DR: The α,β-unsaturated acyl azolium has emerged as a central reactive intermediate for reaction discovery using N-heterocyclic carbene catalysis as discussed by the authors.