One-Pot, Catalyst-Free Synthesis of Nitriles from Aldehydes Using Aminating Reagent MsONH3OTf

Synlett ◽  
2021 ◽  
Author(s):  
Tharcisse Gatera ◽  
Daijiao Zhuang ◽  
Rulong Yan
Keyword(s):  
Functional Group ◽  
Triflic Acid ◽  
One Pot ◽  
Aliphatic Aldehydes ◽  
Mild Conditions ◽  
Catalyst Free ◽  
N Source ◽  
Acid Salts

AbstractAn eco-friendly protocol to synthesize nitriles from their corresponding aromatic and aliphatic aldehydes in excellent yields has been developed. This is a catalyst-free protocol which employs an aminating reagent (MsONH3OTf) under mild conditions. The hydroxylamine triflic acid salts (MsONH3OTf) acted as the N source for this protocol. Our protocol proved to be easy to perform and presented good functional group tolerance.

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>.

scholarly journals Nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts enabled by NN2 pincer ligand

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Xingjie Zhang ◽  
Di Qi ◽  
Chenchen Jiao ◽  
Xiaopan Liu ◽  
Guisheng Zhang
Keyword(s):  
Functional Group ◽  
High Efficiency ◽  
Materials Science ◽  
Alkylating Agents ◽  
Sonogashira Coupling ◽  
Pincer Ligand ◽  
One Pot ◽  
Mild Conditions ◽  
Alkyl Amines ◽  
Sonogashira Reactions

AbstractAlkynes are amongst the most valuable functional groups in organic chemistry and widely used in chemical biology, pharmacy, and materials science. However, the preparation of alkyl-substituted alkynes still remains elusive. Here, we show a nickel-catalyzed deaminative Sonogashira coupling of alkylpyridinium salts. Key to the success of this coupling is the development of an easily accessible and bench-stable amide-type pincer ligand. This ligand allows naturally abundant alkyl amines as alkylating agents in Sonogashira reactions, and produces diverse alkynes in excellent yields under mild conditions. Salient merits of this chemistry include broad substrate scope and functional group tolerance, gram-scale synthesis, one-pot transformation, versatile late-stage derivatizations as well as the use of inexpensive pre-catalyst and readily available substrates. The high efficiency and strong practicability bode well for the widespread applications of this strategy in constructing functional molecules, materials, and fine chemicals.

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2891-2896 ◽  
Author(s):  
Jinna Song ◽  
Xihe Bi ◽  
Qi Zhang ◽  
Kaki Raveendra Babu ◽  
Zhouliang Huang
Keyword(s):  
Visible Light ◽  
Aromatic Compounds ◽  
Functional Group ◽  
Simple Procedure ◽  
One Pot ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Conventional Methods ◽  
Straightforward Approach

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri­hydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

Convenient and efficient synthesis of disubstituted piperazine derivatives by catalyst-free, atom-economical and tricomponent domino reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (14) ◽  
pp. 10768-10772 ◽  
Author(s):  
Hong-Ru Dong ◽  
Zi-Bao Chen ◽  
Rong-Shan Li ◽  
Heng-Shan Dong ◽  
Zhi-Xiang Xie
Keyword(s):  
Free Atom ◽  
Domino Reactions ◽  
Efficient Synthesis ◽  
One Pot ◽  
Diversity Oriented Synthesis ◽  
Mild Conditions ◽  
Catalyst Free ◽  
Piperazine Derivatives ◽  
High Yields

One-pot, atom-economical, catalyst-free and tri-component domino reactions are applied to diversity-oriented synthesis (DOS) of disubstituted piperazine derivatives under mild conditions with moderate to high yields.

Fe(III)/l-Valine-Catalyzed One-Pot Synthesis of N-Sulfinyl- and N-Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides

Synlett ◽  
2018 ◽  
Vol 29 (09) ◽  
pp. 1232-1238
Author(s):  
Guofu Zhang ◽  
Yunzhe Xing ◽  
Shengjun Xu ◽  
Chengrong Ding ◽  
Shang Shan
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Cascade Reaction ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Oxidation Of Alcohols

An efficient Fe(III), l-valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N-sulfinyl- and N-sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.

Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4170-4182 ◽  
Author(s):  
Lin-Lin Zhang ◽  
Ya-Ting Li ◽  
Ting Gao ◽  
Sha-Sha Guo ◽  
Bei Yang ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Functional Group ◽  
High Efficiency ◽  
Efficient Synthesis ◽  
One Pot ◽  
Mild Conditions ◽  
Ligand Free ◽  
Multistep Reaction ◽  
Easy Operation

A sequential multistep reaction toward 5-thio- or 5-selenotriazoles has been established by generation of both copper(I) triazolides and sulfenylating or selenylating agents in situ, starting from elemental sulfur or selenium. This reaction features mild conditions, readily available and broad-scope substrates, good functional group compatibility, high efficiency and regioselectivity, easy operation, and ligand-free CuI.

Additive- and Oxidant-Free Expedient Synthesis of Benzimidazoles Catalyzed by Cobalt Nanocomposites on N-Doped Carbon

Synlett ◽  
2019 ◽  
Vol 30 (03) ◽  
pp. 319-324 ◽  
Author(s):  
Zhaozhan Wang ◽  
Tao Song ◽  
Yong Yang
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Biologically Active ◽  
One Pot ◽  
Mild Conditions ◽  
Wide Range ◽  
High Yields

A one-pot direct synthesis of a wide range of biologically active benzimidazoles through coupling of phenylenediamines and aldehydes catalyzed by a highly recyclable nonnoble cobalt nanocomposite was developed. A broad set of benzimidazoles can be efficiently synthesized in high yields and with good functional-group tolerance under additive- and oxidant-free mild conditions. The catalyst can be easily recycled for successive uses, and the process permits gram-scale syntheses of benzimidazoles.

Ligand- and catalyst-free intramolecular C-S bond formation: direct access to indalothiochromen- 4-ones

2015 ◽  
Vol 21 (3) ◽  
pp. 159-163 ◽  
Author(s):  
T.A. Jenifer Vijay ◽  
Nagarakere C. Sandhya ◽  
C.S. Pavankumar ◽  
Kanchugarakoppal S. Rangappa ◽  
Kempegowda Mantelingu
Keyword(s):  
Functional Group ◽  
Direct Synthesis ◽  
Bond Formation ◽  
Direct Access ◽  
Mild Conditions ◽  
Catalyst Free

AbstractAn efficient ligand- and catalyst-free intramolecular S-arylation leading to the direct synthesis of indalothiochromen-4-ones from simple dithioesters under mild conditions has been developed. This method is particularly noteworthy given its experimental simplicity, high generality, and good functional group toleration.

scholarly journals One-Pot Reductive Acetylation of Aldehydes using 1-Hydrosilatrane in Acetic Acid

SynOpen ◽  
2019 ◽  
Vol 03 (01) ◽  
pp. 1-3 ◽  
Author(s):  
Reuben James ◽  
Sharon Herlugson ◽  
Sami Varjosaari ◽  
Vladislav Skrypai ◽  
Zainab Shakeel ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Organic Synthesis ◽  
Functional Group ◽  
Building Blocks ◽  
Flash Chromatography ◽  
Primary Alcohols ◽  
Facile Synthesis ◽  
One Pot ◽  
Aryl Aldehydes ◽  
Mild Conditions

A one-pot, direct reductive acetylation of aldehydes was achieved under mild conditions using 1-hydrosilatrane as a safe and easily accessible catalyst. Described herein is a facile synthesis that produces acylated primary alcohols that can serve as valuable building blocks for organic synthesis. The method has good functional group tolerance and works for a range of aryl aldehydes, with the notable exception of electron-rich arenes. A library of esters was isolated by flash chromatography in yields as high as 92%.

An ionic liquid catalyzed reusable protocol for one-pot synthesis of 2,3-dihydroquinazolin-4(1H)-one under mild conditions

2015 ◽  
Vol 39 (12) ◽  
pp. 9693-9699 ◽  
Author(s):  
S. Nagarajan ◽  
Tanveer Mahamadali Shaikh ◽  
Elango Kandasamy
Keyword(s):  
Ionic Liquid ◽  
Catalytic Activity ◽  
Functional Group ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Synthetic Utility

This article describes an efficient protocol for the syntheses of 2,3-dihydroquinazolinones. The synthetic utility of this methodology has been demonstrated with 30 different substrates. The reaction showed good functional group tolerance and high levels of catalytic activity.

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