Hydrazo coupling: the efficient transition-metal-free C–H functionalization of 8-hydroxyquinoline and phenol through base catalysis

2019 ◽  
Vol 21 (23) ◽  
pp. 6381-6389 ◽  
Author(s):  
Pavel N. Solyev ◽  
Daria K. Sherman ◽  
Roman A. Novikov ◽  
Eugenia A. Levina ◽  
Sergey N. Kochetkov
Keyword(s):  
Transition Metal ◽  
Base Catalysis ◽  
Metal Free ◽  
Hydrazine Derivatives ◽  
Mild Conditions ◽  
Plausible Mechanism ◽  
Facile Route

A new reaction involving the quantitative coupling of phenolic substrates to azodicarboxylate esters under mild conditions is a facile route for obtaining hydrazine derivatives. A plausible mechanism, catalysts, scope and application are discussed.

A Sequential Ugi-Smiles / Transition-Metal-Free Endo-Dig Conia-ene Cyclization: The Selective Synthesis of Saccharin Substituted 2,5-dihydropyrroles

2021 ◽  
Author(s):  
Hassan Seyrani ◽  
Sorour Ramezanpour ◽  
Aref Vaezghaemi ◽  
Farzad Kobarfard
Keyword(s):  
Transition Metal ◽  
Free Access ◽  
Selective Synthesis ◽  
Metal Free ◽  
Mild Conditions

A convenient, transition-metal-free access to a series of unprecedented saccharin substituted 2,5-dihydropyrroles is reported. This approach employs a post-Ugi-Smiles 5-endo-dig Conia-ene cyclization sequence in mild conditions while incorporating a series...

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

scholarly journals An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade

2021 ◽  
Author(s):  
Philipp Natho ◽  
Zeyu Yang ◽  
Lewis Allen ◽  
Juliette Rey ◽  
Andrew J P White ◽  
...  
Keyword(s):  
Transition Metal ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions

A transition-metal-free strategy for the synthesis of 2-(cyclobut-1-en-1-yl)-1H-indoles under mild conditions is described herein. A series of substituted 2-(cyclobut-1-en-1-yl)-1H-indoles are accessed by a one-pot cyclobutenylation/deprotection cascade from N-Boc protected indoles....

Direct and metal-free oxidative amination of sp3 C–H bonds for the construction of 2-hetarylquinazolin-4(3H)-ones

2016 ◽  
Vol 3 (9) ◽  
pp. 1096-1099 ◽  
Author(s):  
Huanhuan Liu ◽  
Tianran Zhai ◽  
Shiteng Ding ◽  
Yalei Hou ◽  
Xiangyu Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
New Method ◽  
Oxidative Amination ◽  
Metal Free ◽  
Mild Conditions

New method for synthesis of 2-hetarylquinazolin-4(3H)-ones from 2-aminobenzamides and (2-azaaryl)methanes under transition-metal free conditions, featuring a wide substrate scope with a broad range of functional group tolerance under mild conditions.

Regioselective 1,4-conjugate aza-Michael addition of dienones with benzotriazole

2017 ◽  
Vol 23 (4) ◽  
Author(s):  
Zheng Li ◽  
Tianpeng Li ◽  
Rugang Fu ◽  
Jingya Yang
Keyword(s):  
Transition Metal ◽  
Michael Addition ◽  
Potassium Acetate ◽  
High Yield ◽  
Metal Free ◽  
Mild Conditions

AbstractThe regioselective 1,4-conjugate aza-Michael addition of dienones with benzotriazole catalyzed by potassium acetate is described. A series of 3-(benzotriazol-1-yl)-1,5-diarylpent-4-en-1-ones were efficiently synthesized under mild conditions. This protocol has advantages of transition-metal free catalyst, high yield and high regioselectivity.

scholarly journals Photocatalytic Synthesis of Tetra-Substituted Furans Promoted by Carbon Dioxide

2021 ◽  
Author(s):  
Ya-Ming Tian ◽  
Huaiju Wang ◽  
Ritu Ritu ◽  
Burkhard Koenig
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Visible Light ◽  
Metal Free ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Visible Light Driven ◽  
Substituted Furans ◽  
Photocatalytic Synthesis

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that...

scholarly journals Metal Free Amino-Oxidation of Electron Rich Alkenes Mediated by an Oxoammonium Salt

2020 ◽  
Author(s):  
Alexandra Millimaci ◽  
Rowan Meador ◽  
Sara Dampf ◽  
John D. Chisholm
Keyword(s):  
Transition Metal ◽  
Solvent Effects ◽  
Free Amino ◽  
Oxidation Products ◽  
Direct Transition ◽  
Metal Free ◽  
Mild Conditions ◽  
Relative Stereochemistry ◽  
Oxoammonium Salt

<div> <div> <div> <p>4-Acetamido-2,2,6,6-tetramethyl-1-oxopiperidinium tetrafluoroborate (Bobbitt’s salt) effectively activates electron rich alkenes and promotes the addition of anilines. This transformation provides a direct, transition metal free method for amino-oxidation of alkenes under mild conditions. The relative stereochemistry of the amino-oxidation is influenced by solvent effects, with both the syn and anti amino-oxidation products being accessible from identical starting materials. </p> </div> </div> </div>

Transition metal-free oxidative ortho-acylation of phenols with N-heteroarylmethanes via double C–H activation

2016 ◽  
Vol 6 (15) ◽  
pp. 5792-5796 ◽  
Author(s):  
Min Liu ◽  
Tieqiao Chen ◽  
Yongbo Zhou ◽  
Shuang-Feng Yin
Keyword(s):  
Transition Metal ◽  
Metal Free ◽  
Reaction Proceeds ◽  
Plausible Mechanism ◽  
Double Activation

The direct oxidative acylation of phenols with N-heteroarylmethanes via sp3C–H and sp2C–H double activation was achieved under metal-free conditions. The reaction proceeds in a facile I2/DMSO/O2 system regio-selectively to produce valuable (2-hydroxyphenyl)arylmethanones. A plausible mechanism was proposed.

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