One-step chemoselective conversion of tetrahydropyranyl ethers to silyl-protected alcohols

RSC Advances ◽  
2014 ◽  
Vol 4 (28) ◽  
pp. 14475-14479 ◽  
Author(s):  
Julián Bergueiro ◽  
Javier Montenegro ◽  
Carlos Saá ◽  
Susana López
Keyword(s):  
Single Step ◽  
Protecting Groups ◽  
Reaction Conditions ◽  
One Pot ◽  
Silyl Ethers ◽  
Triple Bonds ◽  
Mild Conditions ◽  
Silyl Groups ◽  
One Step ◽  
Optimal Reaction

A novel chemoselective one-pot transformation of acetals to silyl ethers is reported. Free hydroxyls, double bonds and triple bonds are unaffected in optimal reaction conditions. This practical, inexpensive protocol allows the selective replacement of acetal-forming protecting groups with silyl groups in a single step under mild conditions.

scholarly journals Three-component synthesis of highly functionalized aziridines containing a peptide side chain and their one-step transformation into β-functionalized α-ketoamides

2016 ◽  
Vol 12 ◽  
pp. 1772-1777 ◽  
Author(s):  
Lena Huck ◽  
Juan F González ◽  
Elena de la Cuesta ◽  
J Carlos Menéndez
Keyword(s):  
Single Step ◽  
Side Chain ◽  
One Pot ◽  
Aziridine Ring ◽  
Component Process ◽  
Mild Conditions ◽  
One Step

A sequential three-component process is described, starting from 3-arylmethylene-2,5-piperazinediones and involving a one-pot sequence of reactions achieving regioselective opening of the 2,5-diketopiperazine ring and diastereoselective generation of an aziridine ring. This method allows the preparation of N-unprotected, trisubstituted aziridines bearing a peptide side chain under mild conditions. Their transformation into β-trifluoroacetamido-α-ketoamide and α,β-diketoamide frameworks was also achieved in a single step.

One-step Synthesis of β-lactams Using Cyanuric Fluoride

2013 ◽  
Vol 37 (1) ◽  
pp. 25-27 ◽  
Author(s):  
Maaroof Zarei
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
One Step ◽  
Acetic Acids

Cyanuric fluoride works as an efficient acid activator reagent for the direct [2+2] ketene–imine cycloaddition of substituted acetic acids and imines in a one-pot synthesis under mild conditions. The yields are good to excellent and the reaction conditions are mild, simple and efficient.

One-Pot Synthesis of N-Arylated Amines by Hydroaminomethyl­ation of 2,5-Dihydrofuran with Aromatic Amines

Synthesis ◽  
2019 ◽  
Vol 51 (07) ◽  
pp. 1585-1594 ◽  
Author(s):  
Lailai Wang ◽  
Zhiwen Zheng
Keyword(s):  
Catalytic System ◽  
Catalyst Precursor ◽  
Reaction Parameters ◽  
Reaction Conditions ◽  
Phosphorus Ligands ◽  
One Pot ◽  
Cyclic Olefins ◽  
One Step ◽  
Important Intermediate ◽  
Optimal Reaction

A new efficient catalytic system for one-step synthesis of N-arylated amines, for example, an important intermediate, 4-ethyl-N-[(tetrahydrofuran-3-yl)methyl]aniline, is achieved by using different rhodium precursor and phosphorus ligands catalyzed hydroaminomethylation of aniline and its derivatives with heterocyclic and/or cyclic olefins. By screening the reaction parameters, the optimal reaction conditions are found as follows: methanol as a solvent, PPh3 as a ligand, [Rh(cod)2]BF4 as a catalyst precursor, a P/Rh ratio of 5:1, syngas pressure 4 MPa (H2/CO = 3:1), 100 °C, 20 hours, and no additives. The conversion of aniline reaches >99% and the yield of N-[(tetrahydrofuran-3-yl)methyl]aniline is up to 99% using this catalytic system. Moreover, the reaction of aniline and various cyclic olefins is investigated under the optimal conditions, and excellent conversion and good yields are obtained.

Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines

Synlett ◽  
2017 ◽  
Vol 28 (19) ◽  
pp. 2675-2679 ◽  
Author(s):  
Chenghui Sun ◽  
Honggang Liang ◽  
Lingxiang Bao ◽  
Yao Du ◽  
Yiying Zhang ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Substitution Reaction ◽  
Cyanogen Bromide ◽  
New Method ◽  
Nucleophilic Substitution Reaction ◽  
Tertiary Amines ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
One Step

Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan­amides through an N-deallylation reaction and an N-cyanation reaction in one pot.

An Example of Ketone Olefination via Praseodymium-Mediated Barbier Reaction in the Presence of Diethyl Phosphite

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1437-1441
Author(s):  
Xu yan Cao ◽  
Fei Huang ◽  
Songlin Zhang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Type Reaction ◽  
Mild Conditions ◽  
Allyl Halides ◽  
Barbier Reaction

The first example of carbon double-bond formation via praseodymium-mediated Barbier type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported. The reaction is highly α-regioselective and conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with practical reaction conditions.

Neodymium-Promoted Highly Selective Carbon–Carbon Double Bond Formation of Ketones with Allyl Halides in the Presence of Diethyl Phosphite

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3446-3451
Author(s):  
Songlin Zhang ◽  
Dengbing Xie ◽  
Yiqiong Wang ◽  
Bo Yang
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Point Of View ◽  
Diethyl Phosphite ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions ◽  
Carbon Double Bond ◽  
Allyl Halides ◽  
First Time

The carbon–carbon double bond formation via neodymium-mediated Barbier-type reaction of ketones and allyl halides in the presence of diethyl phosphite is reported for the first time. The reaction is highly α-regioselective and was conveniently carried out under mild conditions in a one-pot fashion. From a synthetic point of view, a series of conjugated alkenes were obtained in moderate to good yields in this one-pot reaction with feasible reaction conditions.

Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates

Synlett ◽  
2018 ◽  
Vol 29 (05) ◽  
pp. 668-672 ◽  
Author(s):  
Jianbo Zhang ◽  
Guosheng Sun ◽  
Yue Wu ◽  
Anqi Liu ◽  
Saifeng Qiu ◽  
...  
Keyword(s):  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Optimal Reaction ◽  
Glycosyl Donors

Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective, affordable, and green glycosylation procedure.

Preparation of the Gold Nanoparticles and its Activity for Single-Step Amination of Benzene to Aniline

2013 ◽  
Vol 661 ◽  
pp. 47-52
Author(s):  
Gang Chen ◽  
Chun Hua Yang
Keyword(s):  
Gold Nanoparticles ◽  
Single Step ◽  
Xps Analysis ◽  
Deposition Method ◽  
Reaction Conditions ◽  
Catalyst Amount ◽  
Mild Conditions ◽  
Colloidal Deposition ◽  
Alumina Particles

Gold nanoparticles (AuNPs) were attached to the surface of alumina particles by an in-situ immobilizing method. SEM and XPS analysis showed that the coverage of alumina particles by AuNPs increased as the amount of alumina decreased; AuNPs onto alumina particles by the conventional colloidal deposition method were also prepared, whose TEM showed that the coverage of AuNPs was evidently smaller than that in the case of modified colloidal deposition method，although the AuNPs were spread almost uniformly over the surface of alumina particles. Au-immobilized alumina particles were subsequently utilized as the catalysts for direct amination of benzene with NH3H2O as an aminating agent and H2O2 as an oxidant under mild conditions. The reaction conditions were optimized: when catalyst amount was 2.0 g, reaction temperature was 50 °C, NH3H2O amount was 60 mL, H2O2 amount was 30 mL, and reaction time is 2 h, Au-immobilized alumina particles showed the highest aniline yield (1.96 mg) for 25 mL benzene.

scholarly journals One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

scholarly journals Multicomponent versus domino reactions: One-pot free-radical synthesis of β-amino-ethers and β-amino-alcohols

2015 ◽  
Vol 11 ◽  
pp. 66-73 ◽  
Author(s):  
Bianca Rossi ◽  
Nadia Pastori ◽  
Simona Prosperini ◽  
Carlo Punta
Keyword(s):  
Free Radical ◽  
Cyclic Ether ◽  
Radical Addition ◽  
Domino Reaction ◽  
Alcohol Molecule ◽  
Secondary Products ◽  
Reaction Conditions ◽  
One Pot ◽  
Mild Conditions

Following an optimized multicomponent procedure, an aryl amine, a ketone, and a cyclic ether or an alcohol molecule are assembled in a one-pot synthesis by nucleophilic radical addition of ketyl radicals to ketimines generated in situ. The reaction occurs under mild conditions by mediation of the TiCl4/Zn/t-BuOOH system, leading to the formation of quaternary β-amino-ethers and -alcohols. The new reaction conditions guarantee good selectivity by preventing the formation of secondary products. The secondary products are possibly derived from a competitive domino reaction, which involves further oxidation of the ketyl radicals.

Sign in / Sign up

Export Citation Format

Share Document