Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C–H activation

RSC Advances ◽  
2016 ◽  
Vol 6 (92) ◽  
pp. 89413-89416 ◽  
Author(s):  
Jiajia Gu ◽  
Zheng Fang ◽  
Yuhang Yang ◽  
Zhao Yang ◽  
Li Wan ◽  
...  
Keyword(s):  
Secondary Amines ◽  
One Pot ◽  
Mild Conditions ◽  
Primary And Secondary Amines ◽  
Aromatic Alcohols ◽  
Oxidative Amidation

Copper-catalyzed one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, to form amides under mild conditions.

scholarly journals One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes

2015 ◽  
Vol 13 (34) ◽  
pp. 8993-8995 ◽  
Author(s):  
Vladimir A. Maslivetc ◽  
Marina Rubina ◽  
Michael Rubin
Keyword(s):  
Double Bond ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
One Pot Synthesis ◽  
Primary And Secondary Amines ◽  
Donor Acceptor

A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor–acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.

scholarly journals Straightforward One-Pot Syntheses of Silylamides of Magnesium and Calcium via an In Situ Grignard Metalation Method

Synthesis ◽  
2018 ◽  
Vol 51 (05) ◽  
pp. 1115-1122 ◽  
Author(s):  
Sven Krieck ◽  
Philipp Schüler ◽  
Jan Peschel ◽  
Matthias Westerhausen
Keyword(s):  
Large Scale ◽  
Room Temperature ◽  
Secondary Amines ◽  
Complex Calcium ◽  
One Pot ◽  
Primary And Secondary Amines ◽  
Catalytic Applications

Calcium bis[bis(trimethylsilyl)amide] (Ca(HMDS)2) is a widely used reagent in diverse stoichiometric and catalytic applications. These processes necessitate a straightforward and large-scale access of this complex. Calcium does not react with primary and secondary amines, but the addition of excess bromoethane to a mixture of calcium turnings and amines in THF at room temperature yields the corresponding calcium bis(amides), calcium bromide and ethane. This in situ Grignard metalation method (iGMM) allows the preparation of calcium bis(amides) from secondary and primary trialkylsilyl-substituted amines and anilines on a multigram scale.1 Background2 The In Situ Grignard Metalation Method (iGMM)3 Properties of [(thf)2M(HMDS)2]4 Applications and Perspective

A new approach to arylhydrazides via the reaction of the Mitsunobu reagent with arynes: further application to access diverse nitrogen-containing heterocycles in one pot

2017 ◽  
Vol 4 (8) ◽  
pp. 1636-1639 ◽  
Author(s):  
Bin Cheng ◽  
Bian Bao ◽  
Yanhe Chen ◽  
Ning Wang ◽  
Yun Li ◽  
...  
Keyword(s):  
One Pot ◽  
New Approach ◽  
Mild Conditions ◽  
Highly Active ◽  
Active Intermediates

A new route to arylhydrazides involving the reaction of two highly active intermediates, the 1,3-zwitterion generated in situ from the Mitsunobu reagent and arynes, under mild conditions has been developed.

scholarly journals Rhodium(III)-Catalyzed Three-Component 1,2-Diamination of Unactivated Terminal Alkenes

Synthesis ◽  
2019 ◽  
Vol 52 (08) ◽  
pp. 1247-1252 ◽  
Author(s):  
Sumin Lee ◽  
Young Jin Jang ◽  
Erik J. T. Phipps ◽  
Honghui Lei ◽  
Tomislav Rovis
Keyword(s):  
Good Yield ◽  
Ring Opening ◽  
Secondary Amines ◽  
One Pot ◽  
Rapid Access ◽  
Primary And Secondary Amines ◽  
Terminal Alkenes ◽  
Broad Array ◽  
Vicinal Diamines

We report a three-component diamination of simple unactivated alkenes using an electrophilic nitrene source and amine nucleo­philes. The reaction provides rapid access to 1,2-vicinal diamines from terminal alkenes through a one-pot protocol. The transformation proceeds smoothly with excellent tolerance for a broad array of primary and secondary amines, affording the desired products in good yield and regioselectivity. The mechanism is proposed to proceed through a Rh(III)-catalyzed aziridination of alkenes with subsequent ring opening by primary or secondary amines.

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.

Catalyst-Free One-Pot Reductive Alkylation of Primary and Secondary Amines and N,N-Dimethylation of Amino Acids Using Sodium Borohydride in 2,2,2-Trifluoroethanol

Synthesis ◽  
2010 ◽  
Vol 2011 (03) ◽  
pp. 490-496 ◽  
Author(s):  
Mahmood Tajbakhsh ◽  
Rahman Hosseinzadeh ◽  
Heshmatollah Alinezhad ◽  
Somayeh Ghahari ◽  
Akbar Heydari ◽  
...  
Keyword(s):  
Amino Acids ◽  
Sodium Borohydride ◽  
Secondary Amines ◽  
Reductive Alkylation ◽  
One Pot ◽  
Catalyst Free ◽  
Primary And Secondary Amines

scholarly journals Chemoselective activation of amide carbonyls towards nucleophilic reagents

2016 ◽  
Author(s):  
Bartłomiej Furman
Keyword(s):  
Chemical Biology ◽  
Grignard Reagents ◽  
Synthetic Method ◽  
Important Class ◽  
Selective Activation ◽  
One Pot ◽  
Mild Conditions ◽  
Nucleophilic Reagents ◽  
Danishefsky's Diene

Amides represent an important class of compounds in chemistry, chemical biology and pharmaceutical industry. Their broad utility in many fields is closely tied to the structure of the amide moiety which endows these compounds with unique features. The low reactivity of amide carbonyls towards nucleophiles is a major obstacle to their further functionalization. Selective activation of amides and lactams enables access to novel reactivity pathways and opens up intriguing perspectives in synthesis. Recently, we have demonstrated that upon treatment with Cp2Zr(H)Cl (Schwartz’s reagent), five- and six-membered lactams, including sugar- and hydroxy acid-derived lactams, can be easily converted into imines under mild conditions. In addition, as was also shown, in situ generated cyclic imines can be directly subjected to further reactions with nucleophilic reagents such as allyltributylstannane, Grignard reagents, enolates or Danishefsky’s diene to afford α-functionalized pyrrolidines, piperidines and polyhydroxylated pyrrolidine peptidomimetic scaffolds in a one-pot manner. The key advantage of the presented approach is the simplicity and convenience of generation of sugar-derived imines from readily available starting materials: sugar-derived lactams. The use of sugar-derived lactams as cyclic imine precursors is crucial to the efficiency of the described synthetic method. These compounds are more readily prepared, handled, and stored than the alternative precursors of cyclic imines such as nitrones, N-chloroamines or azido aldehydes. In the second part of the lecture a method for preparing 2,3-disubstituted indoles from commercially available isatins will be briefly presented.

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.

A Facile Approach to Catalyst-Free Cyanation and Azidation of ­Organic Compounds and a One-Pot Preparation of 5-Substituted 1H-Tetrazoles by Using a Dimethyl Sulfoxide–Nitric Acid Combination

Synlett ◽  
2019 ◽  
Vol 30 (20) ◽  
pp. 2290-2294
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Boshra Mahmoudi ◽  
Milad Kazemnejadi
Keyword(s):  
Nitric Acid ◽  
Dimethyl Sulfoxide ◽  
Organic Compounds ◽  
Sodium Azide ◽  
Potassium Cyanide ◽  
Hydroxylamine Hydrochloride ◽  
One Pot ◽  
Mild Conditions ◽  
Tetrazole Derivatives

In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ4-sulfanecarbonitrile or azido(dimethyl)-λ4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide–nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.

Synthesis of α-amino nitriles through one-pot selective Ru-photocatalyzed oxidative cyanation of amines

2020 ◽  
Vol 7 (17) ◽  
pp. 3092-3105 ◽  
Author(s):  
Igor Echevarría ◽  
Mónica Vaquero ◽  
Roberto Quesada ◽  
Gustavo Espino
Keyword(s):  
Secondary Amines ◽  
Excellent Performance ◽  
One Pot ◽  
New Family ◽  
Primary And Secondary Amines

A new family of Ru(ii) photocatalysts exhibits excellent performance in the efficient and eco-friendly one-pot preparation of α-amino nitriles from primary and secondary amines.

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