Recent advances in the direct β-C(sp2)–H functionalization of enamides

Zhu, Tong‐Hao; Xie, Shimin; Rojsitthisak, Pornchai; Wu, Jie

doi:10.1039/c9ob02649e

Cited by 66 publications

(33 citation statements)

References 168 publications

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“…Intrigued by this observation, we first examined the decarboxylative elimination of α-amino acids for the synthesis of enamides, which has been widely used for the preparation of lots of biologically and pharmaceutically important compounds. 14 Notably, Tunge and co-workers reported an elegant dual photoredox/cobalt catalyst system for their synthesis, where the hydrogen atom transfer was achieved by cobalt catalysis. However, this valuable protocol afforded the desired enamides with moderate E / Z ratios ( Scheme 2A ).…”

Section: Resultsmentioning

confidence: 99%

A donor–acceptor complex enables the synthesis of E-olefins from alcohols, amines and carboxylic acids

et al. 2021

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Section: Resultsmentioning

confidence: 99%

A donor–acceptor complex enables the synthesis of E-olefins from alcohols, amines and carboxylic acids

et al. 2021

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“…[38] The reaction proceeds via formation of an acyliminium ion resulting most probably from a single electron transfer process between the radical adduct and the starting iodide 2 followed by elimination of a proton (Scheme 9, frame). [39] Scheme 9. Non-reductive alkylation of 1-vinylpyrrolidin-2-one 12a with iodoesters 2.…”

Section: Resultsmentioning

confidence: 99%

A Giese Reaction for Electron-Rich Alkenes

Hu¹,

Suravarapu²,

Renaud

2020

Preprint

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A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4-tert-butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. The stereoselective hydroalkylation of chiral N-(alk-1-en-1-yl)oxazolidin-2-ones takes place with good to excellent diastereocontrol.

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“…38 The reaction proceeds via formation of an acyliminium ion resulting most probably from a single electron transfer process between the radical adduct and the starting iodide 2 followed by elimination of a proton (Scheme 8, frame). 39 Scheme 8. Non-reductive alkylation of 1-vinylpyrrolidin-2-one 44a with iodoesters 2.…”

Section: Hydroalkylation Of Enamides and Enecarbamatesmentioning

confidence: 99%