Photocatalytic Hydroacylation of Alkenes by Directly Using Acyl Oximes

Zheng, Lan; Xia, Peng-Ju; Zhao, Qinglan; Qian, Yu-En; Jiang, Wen-Nian; Xiang, Hao-Yue; Ye, Hua

doi:10.1021/acs.joc.0c01818

Cited by 31 publications

(13 citation statements)

References 51 publications

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“…Acyl oxime esters could be reduced through single electron transfer in the presence of photocatalyst to yield highly reactive iminyl radicals, which underwent β‐C−C bond fragmentation to disconnect acyl radicals from iminyl radicals through elimination of a nitrile molecule (Scheme 1c). The resulting acyl radicals could be coupled with a wide range of radical acceptors, including alkenes, [15a–c] aromatic rings, [15d] and alkynes [15e–g] . For example, Wu and co‐workers reported a photocatalytic acyl radical cascade reaction between acyl oxime esters with acrylamides and styrenes, respectively [15a] .…”

Section: Methodsmentioning

confidence: 99%

Visible‐Light‐Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation

et al. 2022

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A new photoinduced acylation/arylation of N‐(arylsulfonyl)acrylamide with acyl oxime esters through a nitrogen‐centered radical protocol has been disclosed for efficient preparation of functionalized indolin‐2‐ones, which proceeds through a cascade acyl radical addition of carbon‐carbon double bond, aryl migration, desulfonylation, and intramolecular cyclization sequence. This redox‐neutral strategy features excellent selectivity, good substituent tolerance, and wide substrate scope.

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Section: Methodsmentioning

confidence: 99%

Visible‐Light‐Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation

et al. 2022

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“…For example, Xiao [4] and other chemists [5,7–8] have developed a series of ring‐opening of cycloketone oxime derivatives via NCR strategies. As shown in Scheme 1, Chen (path I), [11a] Wu (path II), [11b] Yang (path III), [11c] and Wu's groups (path IV) [11d] have developed NCR mediated cleavage of carbon‐carbon single bonds in acyl oxime derivatives. In these methods, acyl oxime esters were used as acyl precursors to reat with carbon‐carbon double bonds.…”

Section: Methodsmentioning

confidence: 99%

Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones

et al. 2021

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A nitrogen‐centered radical strategy for the preparation of 3‐acylated spiro[4,5]trienones via visible‐light‐mediated acylation/ipso‐cyclization of alkynes with acyl oxime esters is reported. The alkyl‐ and aryl‐substituted acyl radicals, which generate from the cleavage of carbon‐carbon σ‐bonds in acyl oxime esters via nitrogen‐centered radical pathway, attack the carbon‐carbon triple bonds in propiolamides and then undergo ipso‐cyclization. This method provides a way for the construction of 3‐acyl‐substituted spiro[4,5]trienones, which can introduce aryl‐ or alkyl‐substituted acyl into spiro[4,5]trienone skeletons.

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“…[75] Recently Xiang and co-authors reported the hydroacylation of alkenes 154 using acyloximes 153 as an acylating source under photocatalytic conditions, and it was proposed that phosphoranylradical is a key intermediate for acylation reaction (Scheme 40). [76] 3. Non-Carbonyl Derived Acylating Agents…”

Section: Oximesmentioning

confidence: 99%

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

Sivaraj

Gandhi

2021

Chemistry An Asian Journal

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Functionalizing and derivatising organic molecules is a centerpiece in organic synthesis. Succinctly manipulating and installing acyl moieties in organic molecules spurred the interest of chemists owing to its occurrence in natural products, bioactive molecules, pharmaceuticals, and advanced materials. Traditionally, access to acylation reaction was achieved by Friedel-Crafts reaction, Schotten-Baumann, and Vilsmeier-Haack acylation, however, these protocols own pitfalls. Further to make the acylation process attractive and environmentally friendly, toluene, aldehydes, alcohols, α-keto acids, amines, amides, esters, ethers, nitriles, alkynes, alkenes, ketenes, N-acylbenzotriazoles, ketones, thioacids, oximes, thiazolium carbinols, PIDA, diacyl disulfides and acyl salts were used as an acyl surrogates/reagents. Amusingly, these acylating reagents are considered uncommon and alternative to carboxylic acids, acid chlorides and acetic anhydrides. This short review aims to encompass the usage of acylating agents in transition-metal, metal-free, light-driven and other demanding conditions, and thus reveals their practicality.

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Photocatalytic Hydroacylation of Alkenes by Directly Using Acyl Oximes

Cited by 31 publications

References 51 publications

Visible‐Light‐Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation

Visible‐Light‐Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation

Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones

Alternative and Uncommon Acylating Agents – An Alive and Kicking Methodology

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