KIO3-catalyzed cross dehydrogenative coupling reaction: sulfenylation of phenol and arylamine derivatives in water at room temperature

2019 ◽  
Vol 17 (4) ◽  
pp. 830-834 ◽  
Author(s):  
Dulin Kong ◽  
Tiao Huang ◽  
Min Liang ◽  
Mingshu Wu ◽  
Qiang Lin
Keyword(s):  
Room Temperature ◽  
Coupling Reaction ◽  
Metal Free ◽  
Dehydrogenative Coupling

A metal-free direct sulfenylation of phenol and arylamine derivatives with various heterocyclic thiols and thiones using a cross dehydrogenative coupling protocol in water at room temperature has been developed.

Copper(ii)-catalyzed cross dehydrogenative coupling reaction of N-hydroxyphthalimide with alkanes and ethers via unactivated C(sp3)–H activation at room temperature

RSC Advances ◽  
2016 ◽  
Vol 6 (82) ◽  
pp. 79016-79019 ◽  
Author(s):  
Zhicheng Guo ◽  
Can Jin ◽  
Jiadi Zhou ◽  
Weike Su
Keyword(s):  
Mild Condition ◽  
Room Temperature ◽  
Reaction System ◽  
Coupling Reaction ◽  
Dehydrogenative Coupling

This reaction system shows mild condition and broad substrate scope for generation of O-substituted N-hydroxyphthalimide derivatives via unactivated C(sp3)–H activation.

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

Synthesis ◽  
2019 ◽  
Vol 52 (05) ◽  
pp. 727-734 ◽  
Author(s):  
Farnaz Jafarpour ◽  
Mohammad Asadpour ◽  
Meysam Azizzade ◽  
Mehran Ghasemi ◽  
Saideh Rajai-Daryasarei
Keyword(s):  
Transition Metal ◽  
Room Temperature ◽  
Bond Formation ◽  
Antidepressant Drug ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potential Utility ◽  
Metal Free ◽  
Cross Coupling Reaction ◽  
High Yields

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

Ultrasound accelerated expedient and eco-friendly synthesis of aryl sulfonates using I2 as catalyst at ambient conditions

2021 ◽  
Vol 18 ◽  
Author(s):  
Sha Zhu ◽  
Bin-Bin Wang ◽  
Mei-Chen Tan ◽  
Xiaofu Qian ◽  
Shengneng Ying ◽  
...  
Keyword(s):  
Energy Saving ◽  
Room Temperature ◽  
Coupling Reaction ◽  
Ambient Conditions ◽  
Metal Free ◽  
Mild Conditions ◽  
Efficient Construction ◽  
Ultrasound Assisted

: By using an energy-saving and eco-friendly approach for the efficient construction of aryl sulfonates through ultrasound-assisted coupling reaction of readily sodium sulfinates with N-hydroxyphthalimide was developed under metal-free and mild conditions within 10 min at room temperature.

(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)–H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2432-2436 ◽  
Author(s):  
Can Jin ◽  
Weike Su ◽  
Bin Sun ◽  
Zhiyang Yan
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Coupling Reaction ◽  
Metal Catalyst ◽  
Metal Free ◽  
Alternative Method ◽  
Dehydrogenative Coupling ◽  
Wide Range ◽  
Ready Access

A novel PhI(OAc)2-mediated cross-dehydrogenative coupling reaction of α-C(sp3)–H bonds adjacent to a hetero atom with various azoles has been developed, which provides an alternative method for constructing C–N bonds with high atom efficiency. This new protocol requires no metal catalyst and it provides ready access to a wide range of N-alkylated azole derivatives in moderate to excellent yields by using commercially available PhI(OAc)2 as the sole oxidant. Furthermore, the method is effective on a gram scale, which highlights the practicality of this transformation. The result of radical-captured experiments indicated that the transformation might involve a free-radical pathway.

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