Hyun-Joon Ha · Se In Son · Won Koo Lee · Jieun Choi



Diversely substituted oxindoles were obtained from atom economical direct C–C bond formation reactions of various substituted anilides and pyridinylamides with metal salts and oxides. The catalysts include CuO, Cu2O, FeCl3, Fe2O3, TiO2, ZnO, and Ag2O and their nanoparticles. The reaction proceeds under solvent-free and aerobic conditions in excellent yields. The reaction mechanism was proved to be a single electron transfer pathway with oxygen as the re-oxidant of the metal catalysts.



Graphical abstract: Atom economical synthesis of oxindoles by metal-catalyzed intramolecular C–C bond formation under solvent-free and aerobic conditions

List of Articles
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87 2. a-Lithioamine synthetic equivalents from dipole-stabilized carbaniones: The r-Boc group as an activator for a’-Lithiation of carbamates - Tetrahedron Lett. 1989, 30, 1197 imagefile aziridine 2010-05-06 2336
86 3. a-Lithioamine Synthetic Equivalents: Syntheses of Diastereoisomers from the Boc Piperidines - J. Org. Chem. 1990, 55, 2578 imagefile aziridine 2010-05-06 2840
85 4. Endocyclic Restriction Test: Evaluation of Transition-Structure Geometry for an Aryl Bromide-Alkyllithium Exchange Reaction - J. Am. Chem. Soc. 1990, 112, 1629 imagefile aziridine 2010-05-06 2931
84 5. a-Lithioamine Synthetic Equivalents: Syntheses of Diastereoisomers from Boc Derivatives of Cyclic Amines - J. Org. Chem. 1993, 58, 1109 imagefile aziridine 2010-05-06 3088
83 6. Chirospecific Synthesis of (1S,3R)-l-Amino-3-(hydroxymethyl)cyclopentane a Precursor for Carbocyclic Nucleoside Synthesis. Intramolecular Aziridine Cyclizations - J. Org. Chem. 1993, 58, 5019 imagefile aziridine 2010-05-06 3034
82 7. Regioselective N-Methyl Carbon Lithiation of N-Boc-MethylalkylaminrylamiEnxepae dient Synthesis of Unsymmetrical Amines - Tetrahedron Lett. 1994, 35, 4067 imagefile aziridine 2010-05-06 3136
81 8. Chirospecific Syntheses of Precursors of Cyclopentane and cyclopentene Carbocyclic Nucleosides by [3 + 33-Coupling and Transannular Alkylation - J. Org. Chem. 1995, 60, 4602 imagefile aziridine 2010-05-06 3280
80 9. Resiospecific reductive ring cleavage of N-substituted aziridine-2-carboxylates and an aziridine-2-methanol via catalytic hydrogenation using Pd as a catalyst - Tetrahedron Lett. 1995, 36, 8431 imagefile aziridine 2010-05-06 3166
79 10. Efficient Synthesis of Ephedra Alkaloid Analogues Using an Enantiomerically Pure N-[(R)-(+)-r-Methylbenzyl]aziridine-2-carboxaldehyde - J. Org. Chem. 1996, 61, 6183 imagefile aziridine 2010-05-06 3288
78 11. An Effcient synthesis of both enantiomers of cathinone by regioselective reductive ring opening of substituted aziridines - Tetrahedron 1996, 52, 12111 imagefile aziridine 2010-05-06 3206
77 12. Highly diastereoselective reduction of enantiomerically pure aziridino ketones - Tetrahedron 1996, 52, 12117 imagefile aziridine 2010-05-06 3178
76 13. Efficient Syntheses of (1R,2R)- and (1S,2S)-2-Amino-1-alkyl(oraryl)-1,3-propanediols by Regioselective Ring Opening of Aziridine-2-methanols - J. Org. Chem. .1997, 743 imagefile aziridine 2010-05-12 3646
75 14. A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor - Tetrahedron : Asymmetry 1998, 9, 983 imagefile aziridine 2010-05-12 2998
74 15. Preparation of both (D)- and (L)-serinol derivatives from N-[(S)-a-methylbenzyl]-aziridine-2(S)-methanol - Heterocycles 1998, 48, 1917 imagefile aziridine 2010-05-12 3202
73 16. Synthesis of Substituted (D)-Phenylalanine Derivatives by Regioselective Reduction of Enantiomerically Pure cis-2,3-Disubstituted Aziridines - Tetrahedron Lett. 1998, 39, 9193 imagefile aziridine 2010-05-12 3432
72 17. The Thiazole Route to 2-Formyl-1β-Methylcarbapenem - Bull. Kor. Chem. Soc. 1998, 19, 1294 imagefile aziridine 2010-05-12 3173
71 18. Preparation of Cysteinol Derivatives by Highly Regioselective Ring Opening Nonactivated Chiral Aziridines by Thiols - Tetrahedron 1999, 55, 10041 imagefile aziridine 2010-05-12 3546
70 19. Stereoselective synthesis of protected threo-β-hydroxy-L-glutamic acid using a chiral aziridine - Tetrahedron : Asymmetry 2000, 11, 3283 imagefile aziridine 2010-05-12 3741
69 20. Stereoselective synthesis of enantiomerically pure D-threo-PDMP; manipulation of a core 2,3-diamino alcohol unit - Tetrahedron : Asymmetry 2000, 11, 3283 imagefile aziridine 2010-05-12 3373
68 21. Cycloaddition of Lewis Acid-Induced N-Methyleneanilines as Azadienes to 1,2-Bistrimethylsilyloxycyclobutene and Oxidative Ring Expansion to 1,2,4,5-Tetrahydro-1-benzazocine-3,6-diones - J. Org. Chem. 2000, 65, 8384 imagefile aziridine 2010-05-12 3456
67 22. Selective production of difluoromethyl methyl ether from chlorodifluoromethane using alkali metal carbonates - J. Fluorine Chem. 2001, 107, 133 imagefile aziridine 2010-05-12 4352
66 23. Synthesis of Quaternary Ammoniocephalosporin Having Two Vinyl Groups Using Radical Promoted Thermal Isomerization - Bull. Kor. Chem. Soc. 2001, 22, 659 imagefile aziridine 2010-05-12 3514
65 24. New synthesis and ring opening of cis-3-alkylaziridine-2-carboxylates - Tetrahedron 2001, 57, 9655 imagefile aziridine 2010-05-12 4104
64 25. Asymmetric synthesis of β-amino-α-hydroxy acids through Lewis acid-mediated addition of ketone acetal to imines - Bull. Chem. Soc. Jpn. 2001, 74, 1667 imagefile aziridine 2010-05-12 4138
63 26. New Uses of Amino Acids as Chiral Building Blocks in Organic Synthesis - Org. Lett. 2001, 3, 3119 imagefile aziridine 2010-05-12 3466
62 27. Synthesis of Substituted-(l)-Tryptophanols from an Enantiomerically Pure Aziridine-2-methanol - Org. Lett. 2001, 3, 4197. imagefile aziridine 2010-05-12 3492
61 28. Synthesis and SAR of Aziridinylquinoline-5,8-diones as Agents against Malignant Tumor Cells - Bull. Kor. Chem. Soc. 2001, 22, 1067 imagefile aziridine 2010-05-12 3333
60 29. Syntheses of 1b -Methylcarbapenems Bearing 5-Methyl-4-hydroxypyrrolidinone - Chem. Pharm. Bull. 2002, 50, 415 imagefile aziridine 2010-05-12 3146
59 30. An Efficient Synthesis of N-Boc-D-Diphenylalanine from A Chiral Aziridine-2-Carboxylate - Heterocycles 2002, 57, 1143 imagefile aziridine 2010-05-12 3441


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