SciFinder Page 1

1. Single Step

Overview
Steps/Stages Notes
1.1 no experimental detail, literature preparation,
Reactants: 1, Steps: 1, Stages: 1, Most stages
in any one step: 1

References
A redox-economical synthesis of
trifluoromethylated enamides with the
Langlois reagent
By Yang, Hai-Bin and Selander, Nicklas
From Organic & Biomolecular Chemistry,
15(8), 1771-1775; 2017
CASREACT : Copyright 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
2. Single Step

Overview
Steps/Stages Notes
Reactants: 2, Reagents: 3, Solvents: 2, Steps:
1.1 R:H2NOH-HCl, S:MeOH, 2 h, 70C 1, Stages: 2, Most stages in any one step: 2
1.2 R:Et3N, R:AcCl, S:CH2Cl2, 6 h, 0C References
Divergent Iron-Catalyzed Coupling of O-
Acyloximes with Silyl Enol Ethers
By Yang, Hai-Bin and Selander, Nicklas
From Chemistry - A European Journal, 23(8),
1779-1783; 2017
 SciFinder Page 2
CASREACT : Copyright 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
3. Single Step

Overview
Steps/Stages Notes
literature preparation, Reactants: 2, Reagents:
1.1 R:H2NOH-HCl 1, Steps: 1, Stages: 1, Most stages in any one
step: 1

References
Internal Oxidant-Triggered Aerobic
Oxygenation and Cyclization of Indoles under
Copper Catalysis
By Huang, Huawen et al
From Angewandte Chemie, International
Edition, 55(1), 307-311; 2016
CASREACT : Copyright 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
4. 2 Steps

[Step 2.1]

Overview
Steps/Stages Notes
 SciFinder Page 3
Reactants: 2, Reagents: 3, Solvents: 3, Steps:
1.1 R:AcONa, R:H2NOH-HCl, S:H2O, S:EtOH, 6-8 h, 100C 2, Stages: 3, Most stages in any one step: 2
2.1 S:CH2Cl2, 24 h, rt
References
2.2 R:NaHCO3, rt, neutralized Iron-Catalyzed Synthesis of 2H-Imidazoles
from Oxime Acetates and Vinyl Azides under
Redox-Neutral Conditions
By Zhu, Zhongzhi et al
From Organic Letters, 19(6), 1370-1373;
2017
CASREACT : Copyright 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
5. 2 Steps

[Step 2.1]

Overview
Steps/Stages Notes
Reactants: 2, Reagents: 2, Catalysts: 1,
1.1 R:C5H5N, R:H2NOH-HCl, S:EtOH, 1 h, 60C Solvents: 3, Steps: 2, Stages: 3, Most stages
1.2 S:H2O in any one step: 2
2.1 C:4-DMAP, S:C5H5N, 1 h, rt
References
Copper-Catalyzed Radical/Radical Csp3-H/P-
H Cross-Coupling: -Phosphorylation of Aryl
Ketone O-Acetyloximes
By Ke, Jie et al
From Angewandte Chemie, International
Edition, 54(22), 6604-6607; 2015
Reaction Protocol
Procedure 1. Add NH2OHHCl (2.29 g, 33.0 mmol) in one portion to a solution of propiophenone (22.0 mmol) and
pyridine (5.0 mL, 61.8 mmol) in EtOH (10 mL).
2. Stir the reaction mixture at 60 C for 1 hour.

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CASREACT : Copyright 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.