2023
DOI: 10.1039/d3gc00728f
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Electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides to brominated 2-azaspiro[4.5]decanes

Abstract: An electrochemical electrophilic bromination/spirocyclization of N-benzyl-acrylamides with 2-bromoethan-1-ol as the brominating reagent has been developed. The paired electrolysis employs low concentrations of bromine produced from both cathodic reduction and anodic...

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Cited by 48 publications
(24 citation statements)
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“…This analysis aimed to determine the bonding nature of the compounds as well. 10–13 By employing GGA (generalized gradient approximation) and GGA + U methods, researchers analyzed the optical properties of several systems including rare earth. 14–17 It was found that the TB-mBJ approximation of the TB-mBJ potential is better suited for systems lacking correlated electrons, such as insulators and semiconductors.…”
Section: Introductionmentioning
confidence: 99%
“…This analysis aimed to determine the bonding nature of the compounds as well. 10–13 By employing GGA (generalized gradient approximation) and GGA + U methods, researchers analyzed the optical properties of several systems including rare earth. 14–17 It was found that the TB-mBJ approximation of the TB-mBJ potential is better suited for systems lacking correlated electrons, such as insulators and semiconductors.…”
Section: Introductionmentioning
confidence: 99%
“…Inspired by the primary results of this photocatalytic oxidation of biaryl ynones, we next took the challenge of implementation of this strategy to other ynone systems ( 4 ) . Biphenyl N -arylpropiolamides are susceptible to exhibit synthetic versatility in radical chemistry and theoretically capable to undergo [1,1], [1,2], [1,5], and [2,5] cyclizations; some of the possibilities are designed in Figure and details in Supporting Information.…”
Section: Resultsmentioning
confidence: 99%
“…7, 172.1, 147.2, 146.3, 132.8, 130.5, 64.0, 52.7, 49.1, 25.5, 24.9, 24.5, 24.3, 13.6 . 14 The title compound was prepared according to the general procedure and obtained as a white solid (41 mg, yield: 63%. ); 1 H NMR (400 MHz, CDCl 3 ) δ 7.10 (dd, J = 10.3, 3.0 Hz,1H),6.91 (dd,J = 10.3,3.0 Hz,1H),6.46 (dd,J = 10.3,1.9 Hz,1H),6.39 (dd,J = 10.3,1.9 Hz,1H),3H), 3.37 (d,J = 10.4 Hz,1H), 1.43 (s, 9H), 1.32 (s, 3H); 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 184.…”
Section: ′-(Tert-butyl)-4′-(iodomethyl)-4′-methyl-4h-spiro[naphthalen...mentioning
confidence: 99%