Synthesis of Sulfoximidoyl-Containing Hypervalent Iodine(III) Reagents and Their Use in Transition-Metal-Free Sulfoximidations of Alkynes

2016 ◽  
Vol 128 (41) ◽  
pp. 12845-12848 ◽  
Author(s):  
Han Wang ◽  
Ying Cheng ◽  
Peter Becker ◽  
Gerhard Raabe ◽  
Carsten Bolm
Keyword(s):  
Transition Metal ◽  
Hypervalent Iodine ◽  
Metal Free

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Transition‐Metal‐Free Hypervalent Iodine(III) Reagent‐Promoted Site‐Selective Solid‐Phase Synthesis of Mononitroarylamines

2018 ◽  
Vol 3 (45) ◽  
pp. 12946-12950 ◽  
Author(s):  
Delie An ◽  
Wenkang Song ◽  
Zhihong Peng ◽  
Yingjun Zhang ◽  
Wanrong Dong
Keyword(s):  
Transition Metal ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Hypervalent Iodine ◽  
Phase Synthesis ◽  
Metal Free ◽  
Site Selective

scholarly journals Straightforward Strategies for the Preparation of NH-Sulfox­imines: A Serendipitous Story

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2525-2538 ◽  
Author(s):  
James Bull ◽  
Renzo Luisi ◽  
Leonardo Degennaro
Keyword(s):  
Transition Metal ◽  
Physicochemical Properties ◽  
Direct Synthesis ◽  
Transition Metal Catalysts ◽  
Hypervalent Iodine ◽  
Reaction Conditions ◽  
One Pot ◽  
Metal Free ◽  
Recent Developments ◽  
New Procedures

Sulfoximines are emerging as valuable new isosteres for use in medicinal chemistry, with the potential to modulate physicochemical properties. Recent developments in synthetic strategies have made the unprotected ‘free’ NH-sulfoximine group more readily available, facilitating further study. This account reviews approaches to NH-sulfoximines, with a focus on our contribution to the field. Starting from the development of catalytic strategies involving transition metals, more sustainable metal-free processes have been discovered. In particular, the use of hypervalent iodine reagents to mediate NH-transfer to sulfoxides is described, along with an assessment of the substrate scope. Furthermore, a one-pot strategy to convert sulfides directly into NH-sulfoximines is discussed, with N- and O-transfer occurring under the reaction conditions. Mechanistic evidence for the new procedures is included as well as relevant synthetic applications that further exemplify the potential of these approaches.1 Introduction2 Strategies to Form NH-Sulfoximines Involving Transition-Metal Catalysts3 Metal-Free Strategies to Prepare NH-Sulfoximines4 Mechanistic Evidence for the Direct Synthesis of NH-Sulfoximines from Sulfoxides and Sulfides5 Further Applications6 Conclusion

scholarly journals Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes

2018 ◽  
Vol 16 (41) ◽  
pp. 7561-7563
Author(s):  
J. Schörgenhumer ◽  
M. Waser
Keyword(s):  
Transition Metal ◽  
Hypervalent Iodine ◽  
Terminal Alkynes ◽  
Metal Free ◽  
Catalyst Free

Unsymmetrical 1,3-diynes can easily be accessed under catalyst-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.

Synthesis of Sulfoximidoyl-Containing Hypervalent Iodine(III) Reagents and Their Use in Transition-Metal-Free Sulfoximidations of Alkynes

2016 ◽  
Vol 55 (41) ◽  
pp. 12655-12658 ◽  
Author(s):  
Han Wang ◽  
Ying Cheng ◽  
Peter Becker ◽  
Gerhard Raabe ◽  
Carsten Bolm
Keyword(s):  
Transition Metal ◽  
Hypervalent Iodine ◽  
Metal Free

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

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