Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature

2017 ◽  
Vol 15 (15) ◽  
pp. 3165-3169 ◽  
Author(s):  
Ming-Tao Chen ◽  
Xia You ◽  
Li-Gang Bai ◽  
Qun-Li Luo
Keyword(s):  
Room Temperature ◽  
Trialkyl Phosphite ◽  
Metal Free ◽  
Mild Conditions ◽  
Short Time

Heteroarene N-oxides were successfully converted to heteroarylphosphonates in a very short time under mild conditions through in situ activation with CBrCl3.

scholarly journals Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

2017 ◽  
Vol 13 ◽  
pp. 2023-2027 ◽  
Author(s):  
Hao Wang ◽  
Cui Chen ◽  
Weibing Liu ◽  
Zhibo Zhu
Keyword(s):  
Room Temperature ◽  
Synthetic Methods ◽  
Chemical Modifications ◽  
One Pot ◽  
Butyl Hydroperoxide ◽  
Radical Intermediates ◽  
Mild Conditions ◽  
Tert Butyl Hydroperoxide ◽  
Potential Applications

We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(tert-butylperoxy)-2-iodoethanes, which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(tert-butylperoxy)-2-iodoethanes have several potential applications and allow further chemical modifications, enabling the preparation of synthetically valuable molecules.

Organic Photoredox Catalysis for Pschorr Reaction: A Metal-Free and Mild Approach to 6H-Benzo[c]chromenes

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2311-2315 ◽  
Author(s):  
Gaofeng Feng ◽  
Jing-Yao He ◽  
Qi-Fan Bai ◽  
Chengan Jin
Keyword(s):  
Diazonium Salts ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Synthetic Route ◽  
Metal Free ◽  
Mild Conditions ◽  
Pschorr Reaction

An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6H-benzo[c]chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. The diazonium salts can be either preformed or generated in situ from the corresponding amines with t-BuONO. The process is amenable to gram-sale synthesis of 6H-benzo[c]chromenes, which can be further transformed into both 6H-benzo[c]chromen-6-ones through oxidation or to 6H-benzo[c]chromen-6-amine through sp3 C–H bond amination. The protocol provides an attractive route for the synthesis of a library of 6H-benzo[c]chromes.

Substrate selective synthesis of pyrazolo[1,5-a]pyridines through [3 + 2] cycloaddition of N-aminopyridines and β-nitro styrenes

RSC Advances ◽  
2015 ◽  
Vol 5 (53) ◽  
pp. 42961-42964 ◽  
Author(s):  
Chitrakar Ravi ◽  
Darapaneni Chandra Mohan ◽  
N. Naresh Kumar Reddy ◽  
Subbarayappa Adimurthy
Keyword(s):  
Selective Synthesis ◽  
Metal Free ◽  
Mild Conditions

Synthesis of 2 or 3-(hetero)aryl pyrazolo[1,5-a]pyridines through [3 + 2] cycloaddition ofN-aminopyridine with β-nitrostyrenes followed byin situdenitration under metal-free and mild conditions are described.

scholarly journals REGIOSELECTIVE AND FACILE OXIDATIVE THIOCYANATION OF ANILINES AND INDOLES WITH TRANS-3,5‐DIHYDROPEROXY‐3,5‐DIMETHYL‐1,2‐DIOXOLANE

2014 ◽  
Vol 10 (8) ◽  
pp. 3088-3096 ◽  
Author(s):  
Davood Azarifar ◽  
Maryam Golbaghi ◽  
Mahtab Pirveisian ◽  
Zohreh Najminejad
Keyword(s):  
Room Temperature ◽  
Reaction Times ◽  
Sodium Thiocyanate ◽  
Oxidative Potential ◽  
Mild Conditions ◽  
In Situ Generation

Oxidative potential of trans‐3,5‐dihydroperoxy‐3,5‐dimethyl‐1,2‐dioxolane (DHPODMDO) has been explored in the facile thiocyanation of anilines and indoles through the efficient and in situ generation of SCN+ ion from sodium thiocyanate. The reactions proceed with regioselectivity under mild conditions at room temperature to afford the respective thiocyanate derivatives in excellent yields and low reaction times.

scholarly journals Organophotoredox-Catalyzed Direct C-H Functionalization of “Drug Prejudice” at Room Temperature

2020 ◽  
Author(s):  
Narendra Chaubey ◽  
Anant Kapdi ◽  
Biswanath Maity
Keyword(s):  
Room Temperature ◽  
Bond Functionalization ◽  
First Report ◽  
Metal Free ◽  
Mild Conditions ◽  
The Past ◽  
Free Environment

<p>Organophotocatalytic C─H bond functionalization has attracted lot of attention in the past several years due to the possibility of catalysing reactions in a metal-free environment. Continuing on these lines, we repot herein an organophotoredox catalyzed C─H functionalization of imidazo[1,2-a]pyridines and related heterocycles with malonates under mild conditions providing excellent yields of the products at room temperature. Although, C─3 functionalization of imidazo[1,2-a]pyridines are known, this is the first report involving malonates as coupling partners leading to the synthesis of a range of functionalized products including Zolpidem, a sedative-hypnotic medicine. </p>

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.

[bmim]PF6/KOH: A Recyclable Catalytic System for an Azide–Arylacetaldehyde [3 + 2] Cycloaddition

2017 ◽  
Vol 41 (11) ◽  
pp. 631-635
Author(s):  
Yuqin Jiang ◽  
Kai Wu ◽  
Xuxia Tan ◽  
Dandan Zhang ◽  
Wenpei Dong ◽  
...  
Keyword(s):  
Transition Metal ◽  
Organic Solvent ◽  
Catalytic System ◽  
Room Temperature ◽  
Reaction Medium ◽  
Metal Catalyst ◽  
Transition Metal Catalyst ◽  
Green Protocol ◽  
Mild Conditions

A fast and green protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from azides and arylacetaldehydes at room temperature was developed using [bmim]PF6/KOH as the reaction medium. It was found that the in situ-generated carbene from [bmim]PF6/KOH acted as the catalyst. In the absence of a transition-metal catalyst and organic solvent, this azide–arylacetaldehyde [3 + 2] cycloaddition proceeds efficiently, with high levels of regioselectivity, broad range of substrates, excellent yields and simple operation under mild conditions.

An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1071-1075 ◽  
Author(s):  
Vit Lellek ◽  
Cheng-yi Chen ◽  
Wanggui Yang ◽  
Jie Liu ◽  
Xuebao Ji ◽  
...  
Keyword(s):  
Efficient Synthesis ◽  
One Pot ◽  
Metal Free ◽  
Mild Conditions ◽  
Free Process ◽  
One Pot Condensation ◽  
Substituted Pyrazoles

An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubstituted or 3,4,5-trisubstituted pyrazoles by simply heating pyrazolines in DMSO under oxygen.

Metal-free [3+2] cycloaddition of azides with Tf2CCH2 for the regioselective preparation of elusive 4-(trifluoromethylsulfonyl)-1,2,3-triazoles

2015 ◽  
Vol 51 (32) ◽  
pp. 6992-6995 ◽  
Author(s):  
Benito Alcaide ◽  
Pedro Almendros ◽  
Carlos Lázaro-Milla
Keyword(s):  
Room Temperature ◽  
Metal Free

1,2-Dipole Tf2CCH2 is generated in situ from 2-(2-fluoro-pyridin-1-ium-1-yl)-1,1-bis[(trifluoromethyl)-sulfonyl]ethan-1-ide and immediately reacted at room temperature with azides to afford previously unknown 4-trifluoromethanesulfonyl 1,2,3-triazoles in a highly regio- and chemoselective fashion.

A Fortuitous, Mild Catalytic Carbon–Carbon Bond Hydrogenolysis by a Phosphine-Free Catalyst

2016 ◽  
Vol 69 (5) ◽  
pp. 561 ◽  
Author(s):  
Loorthuraja Rasu ◽  
Ben Rennie ◽  
Mark Miskolzie ◽  
Steven H. Bergens
Keyword(s):  
Low Temperature ◽  
Room Temperature ◽  
Nmr Studies ◽  
Carbon Bond ◽  
Mild Conditions ◽  
Carbon Carbon Bond ◽  
Diamine Ligands ◽  
Insight Into

The putative catalyst trans-[Ru((S,S)-skewphos)(H)2((R,R)-dpen)] (skewphos = 2,4-bis(diphenylphosphino)pentane; dpen = 1,2-diphenylethylenediamine) transforms the trifluoroacetyl amide 2,2,2-trifluoro-1-(piperidin-1-yl)ethanone under mild conditions (4 atm H2, room temperature, 4–24 h, 1 mol-% Ru, 15 mol-% KOtBu in tetrahydrofuran) to generate the formylated amine 1-formylpiperidine and fluoroform via C–C bond hydrogenolysis. Catalysts are also prepared by reacting cis-[Ru(η3-C3H5)(MeCN)2(COD)]BF4 (COD = 1,5-cyclooctadiene) with diamine ligands in situ. Low-temperature NMR studies provided insight into this reaction.

Sign in / Sign up

Export Citation Format

Share Document