Amine-catalyzed and functional group-controlled chemo- and regioselective synthesis of multi-functionalized CF3-benzene via a metal-free process

2019 ◽  
Vol 21 (22) ◽  
pp. 6179-6186 ◽  
Author(s):  
Fu Peng ◽  
Qian Zhao ◽  
Wei Huang ◽  
Shuai-Jiang Liu ◽  
Ya-Jun Zhong ◽  
...  
Keyword(s):  
Functional Group ◽  
Regioselective Synthesis ◽  
Substituted Benzenes ◽  
Metal Free ◽  
Free Process ◽  
Novel Strategy

A novel strategy for the synthesis of CF3-containing multi-substituted benzenes with high chemo- and regioselectivities under metal-free and air-tolerant conditions was established.

Transition-metal-free regioselective synthesis of alkylboronates from arylacetylenes and vinyl arenes

2016 ◽  
Vol 18 (4) ◽  
pp. 932-936 ◽  
Author(s):  
Kai Yang ◽  
Qiuling Song
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Regioselective Synthesis ◽  
Metal Free

A transition-metal-free synthesis of alkylboronates from arylacetylenes or vinyl arenes and B2pin2via tandem borylation and protodeboronation has been developed. This reaction features with excellent regioselectivities, broad functional group tolerance and good yields in both small and gram scale.

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

Oxidative Alkylation/Alkynylation of Terminal Alkenes via Alkylaldehyde Decarbonylation and 1,2-Alkynyl Migration

2021 ◽  
Author(s):  
Jiajia Zhang ◽  
De Chen ◽  
yiqun qin ◽  
Wei Deng ◽  
Yongyue luo ◽  
...  
Keyword(s):  
Functional Group ◽  
Quaternary Carbon ◽  
Metal Free ◽  
Terminal Alkenes ◽  
Oxidative Alkylation

A metal-free oxidative alkene alkylation/alkynylation of 1,4-enyn-3-ols with alkylaldehydes has been achieved, which offers a general access to the challenging quaternary carbon-containing but-3-yn-1-ones. The method features with excellent functional group...

Electrochemical-induced synthesis of quinazolinones via cathode hydration of o-aminobenzonitriles in aqueous solution

2021 ◽  
Author(s):  
Li Yang ◽  
Huiqing Hou ◽  
Lan Li ◽  
Jin Wang ◽  
Sunying Zhou ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Transition Metal ◽  
Metal Free ◽  
Free Process

An efficient and practical electrochemical-catalyzed transition metal-free process for the synthesis of substituted quinazolinones from simple and readily available o-aminobenzonitriles and aldehydes in water has been accomplished. I2/base and water...

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.

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N-Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Yadong Sun ◽  
Ablimit Abdukader ◽  
Yuhan Lu ◽  
Chenjiang Liu
Keyword(s):  
Transition Metal ◽  
Efficient Method ◽  
Room Temperature ◽  
Functional Group ◽  
Ammonium Thiocyanate ◽  
Potassium Persulfate ◽  
Sulfur Source ◽  
Coupling Reactions ◽  
Wide Scope ◽  
Metal Free

AbstractA highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of substrates and good functional-group tolerance. This protocol can be scaled up to a gram level and can be applied to coupling reactions with 4-(4-bromophenyl)-1,2,3-thiadiazole as the substrate.

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Synthesis ◽  
2021 ◽  
Author(s):  
Yury N. Kotovshchikov ◽  
Stepan S. Tatevosyan ◽  
Gennadij V. Latyshev ◽  
Nikolay V. Lukashev ◽  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Cost Effective ◽  
Reductive Cleavage ◽  
Effective Procedure ◽  
Free Base ◽  
Metal Free ◽  
Fused Heterocycles ◽  
Convenient Approach

AbstractA convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Iodine-mediated C–N and C–S bond formation: regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazoles

2017 ◽  
Vol 41 (1) ◽  
pp. 75-80 ◽  
Author(s):  
Sethurajan Ambethkar ◽  
Muthalu Vellimalai ◽  
Vediappen Padmini ◽  
Nattamai Bhuvanesh
Keyword(s):  
Reaction Time ◽  
Intramolecular Cyclization ◽  
Simple Procedure ◽  
Bond Formation ◽  
Molecular Iodine ◽  
Regioselective Synthesis ◽  
Thiazole Derivatives ◽  
Short Reaction Time ◽  
Metal Free

The regioselective synthesis of benzo[4,5]imidazo[2,1-b]thiazole derivatives via amination (C–N) and intramolecular cyclization (C–S) reactions in the presence of molecular iodine has been reported. This method is base and metal free and features inexpensive catalysts, with a simple procedure and a short reaction time.

ChemInform Abstract: Regioselective Synthesis of 1,3,5-Substituted Benzenes via the InCl3/2-Iodophenol-Catalyzed Cyclotrimerization of Alkynes.

ChemInform ◽  
2012 ◽  
Vol 43 (8) ◽  
pp. no-no
Author(s):  
Yan-li Xu ◽  
Ying-ming Pan ◽  
Qiang Wu ◽  
Heng-shan Wang ◽  
Pei-zhen Liu
Keyword(s):  
Regioselective Synthesis ◽  
Substituted Benzenes

scholarly journals Icilio Guareschi and his amazing “1897 reaction”

2021 ◽  
Vol 17 ◽  
pp. 1335-1351
Author(s):  
Gian Cesare Tron ◽  
Alberto Minassi ◽  
Giovanni Sorba ◽  
Mara Fausone ◽  
Giovanni Appendino
Keyword(s):  
Organic Chemistry ◽  
Water Solution ◽  
Applied Science ◽  
History Of Chemistry ◽  
Metal Free ◽  
Free Process ◽  
History Of ◽  
Neutral Water

Organic chemistry honors Icilio Guareschi (1847–1918) with three eponymic reactions, the best known ones being the Guareschi synthesis of pyridones and the Guareschi–Lustgarten reaction. A third Guareschi reaction, the so-called “Guareschi 1897 reaction”, is one of the most unusual reactions in organic chemistry, involving the radical-mediated paradoxical aerobic generation of hydrocarbons in near-neutral water solution. A discussion of the mechanism of this amazing reaction, the only metal-free process that generates hydrocarbons, and the implications of the approach in biology and geosciences mirrors the multifaceted scientific personality of the discoverer. Thus, Guareschi’s eclectic range of activities spans a surprising variety of topics, overcoming the boundaries of the traditional partition of chemistry into organic, inorganic, and analytical branches and systematically crosses the divide between pure and applied science as well as between the history of chemistry and the personal contributions to its development.

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