Nitrogenation of Alkynes with Nitrones to Prepare Functionalized [1,4]Oxazinones through Csp–Csp2 Bond Cleavage DOI
Yu Zhao, L. Yan,

Lin-Fen Liao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9541 - 9546

Published: Oct. 25, 2024

Herein, we report a novel strategy of hypervalent iodine(III) compound-mediated selective Csp–Csp2 bond cleavage alkynes and C═N/N–O nitrones recombination C–C/C–O/C–N multiple bonds to access various functionalized [1,4]oxazinones bearing vicinal carbon stereocenter in good yields high diastereoselectivity. Mechanistic studies revealed that the reaction undergoes domino [4 + 3] cycloaddition, 1,3-rearrangement N–O bond, intramolecular cyclization, dearomatization, rearomatization over four steps single flask. The present method features functional group tolerance, broad substrate scope, C–C/C═N/N–O recombination.

Language: Английский

Palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles DOI
Ning Zhang,

Guojuan Liang,

Dexin Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles is described. variety new 3-carboxamide-3-allylation an all-carbon quaternary center were obtained in moderate to good yields (up 99%). In addition, the asymmetric version this reaction was also explored, providing enantioselectivity.

Language: Английский

Citations

0
Building an All Carbon Quaternary Center via Redox-Neutral Geminal Dual C–H Functionalization of Oxindoles DOI

Priyankar Jha,

Saddam Husen,

Ravindra Kumar

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 18, 2025

Reported here is a catalytic redox-neutral geminal dual C-H functionalization of oxindoles with two distinct aromatics using anilines. The reaction proceeded through pluripotent tetra-substituted alkene intermediate via an extended resonance stabilized carbocation. It furnished wide chemical space around the generation all carbon quaternary centers (>35 examples) in good to excellent yields. developed process highly regioselective and scalable, conditions are environmentally benign nature.

Language: Английский

Citations

0
Organoiodine Catalysed Intramolecular C−N bond Oxidative Coupling for the Synthesis of 3‐Monosubstituted Oxindoles DOI Open Access
Jin‐Tao Yu, Yue Wang,

Jichen Yin

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 14, 2024

Abstract An efficient organoiodine‐catalysed intramolecular direct C−N bond oxidative coupling reaction is presented. Structurally diverse 3‐(mono)substituted oxindoles were rapidly obtained in a complex system up to 87 % yield. Various N ‐alkoxy‐2‐phenylpropanamides well‐tolerated. This study showed that the electronic effects on aromatic ring of reactants have crucial effect selectivity (C−N/C−O) cyclisation products. In addition, gram‐scale synthesis and late‐stage modification oxindole derivatives revealed practical application this transformation.

Language: Английский

Citations

1
Nitrogenation of Alkynes with Nitrones to Prepare Functionalized [1,4]Oxazinones through Csp–Csp2 Bond Cleavage DOI
Yu Zhao, L. Yan,

Lin-Fen Liao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(44), P. 9541 - 9546

Published: Oct. 25, 2024

Herein, we report a novel strategy of hypervalent iodine(III) compound-mediated selective Csp–Csp2 bond cleavage alkynes and C═N/N–O nitrones recombination C–C/C–O/C–N multiple bonds to access various functionalized [1,4]oxazinones bearing vicinal carbon stereocenter in good yields high diastereoselectivity. Mechanistic studies revealed that the reaction undergoes domino [4 + 3] cycloaddition, 1,3-rearrangement N–O bond, intramolecular cyclization, dearomatization, rearomatization over four steps single flask. The present method features functional group tolerance, broad substrate scope, C–C/C═N/N–O recombination.

Language: Английский

Citations

0