scholarly journals Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts: New Entries to Aromatic Amides

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2957
Author(s):  
Satenik Mkrtchyan ◽  
Michał Jakubczyk ◽  
Suneel Lanka ◽  
Michael Pittelkow ◽  
Viktor O. Iaroshenko
Keyword(s):  
Boronic Acids ◽  
Synthetic Methodology ◽  
Sulfonium Salts ◽  
Direct Arylation ◽  
Guided Discovery ◽  
Electronic Nature ◽  
Wide Range ◽  
Tertiary Amides

We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2,2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2,2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.

Chiral [2.2.2] Dienes as Ligands for Rh(I) in Conjugate Additions of Boronic Acids to a Wide Range of Acceptors

2004 ◽  
Vol 6 (21) ◽  
pp. 3873-3876 ◽  
Author(s):  
Christian Defieber ◽  
Jean-François Paquin ◽  
Sonia Serna ◽  
Erick M. Carreira
Keyword(s):  
Boronic Acids ◽  
Conjugate Additions ◽  
Wide Range

Copper-Catalyzed One-Pot Synthesis of Chalcogen-Benzothiazoles/Imidazo[1,2-a]pyridines with Sulfur/Selenium Powder and Aryl Boronic Acids

Synlett ◽  
2018 ◽  
Vol 29 (11) ◽  
pp. 1530-1536 ◽  
Author(s):  
Tao Guo ◽  
Shu-Lei Han ◽  
Yong-Cheng Ma ◽  
Xu-Ning Wei ◽  
Ying-Li Zhu ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Breast Cancer Cell ◽  
Functional Group ◽  
Biological Evaluation ◽  
Boronic Acids ◽  
Breast Cancer Cell Lines ◽  
One Pot ◽  
Wide Range ◽  
Antiproliferative Activities

An efficient and convenient copper-catalyzed oxidative chalcogenation of benzothiazoles and imidazo[1,2-a]pyridines with sulfur/selenium powder and aryl boronic acids was developed. This procedure allows access to a wide range of structurally diverse arylchalcogen-substituted benzothiazoles/imidazo[1,2-a]pyridines in good yields and with good functional group tolerance. A biological evaluation revealed that some of the obtained products exhibited in vitro antiproliferative activities on human-derived lung, stomach, esophageal, and breast cancer cell lines.

ChemInform Abstract: Direct Arylation of Benzothiazoles and Benzoxazoles with Aryl Boronic Acids.

ChemInform ◽  
2011 ◽  
Vol 42 (21) ◽  
pp. no-no
Author(s):  
Sadananda Ranjit ◽  
Xiaogang Liu
Keyword(s):  
Boronic Acids ◽  
Direct Arylation

scholarly journals 2-Aminoquinazolines by Chan–Evans–Lam Coupling of Guanidines with (2-Formylphenyl)boronic Acids

Synlett ◽  
2020 ◽  
Vol 31 (15) ◽  
pp. 1507-1510
Author(s):  
Aigars Jirgensons ◽  
Vitalii V. Solomin ◽  
Alberts Seins
Keyword(s):  
Boronic Acids ◽  
New Method ◽  
Mild Conditions ◽  
Wide Range

A new method is presented for the synthesis of 2-aminoquinazolines, which is based on a Chan–Evans–Lam coupling of (2-formylphenyl)boronic acids with guanidines. Relatively mild conditions involving the use of inexpensive CuI as a catalyst and methanol as a solvent permit the application of the method to a wide range of substrates. Nonsubstituted, N-monosubstituted, and N,N-disubstituted guanidines can be used as reactants to give the corresponding 2-aminoquinazolines in moderate yields from readily available (2-formylphenyl)boronic acids.

scholarly journals Genome-guided Discovery of the First Myxobacterial Biarylitide Myxarylin Reveals Distinct C–N Biaryl Crosslinking in RiPP Biosynthesis

2021 ◽  
Author(s):  
Joachim J. Hug ◽  
Nicolas A. Frank ◽  
Christine Walt ◽  
Petra Šenica ◽  
Fabian Panter ◽  
...  
Keyword(s):  
Amino Acids ◽  
Posttranslational Modifications ◽  
Myxococcus Xanthus ◽  
Aromatic Amino Acids ◽  
Diverse Group ◽  
Guided Discovery ◽  
Wide Range ◽  
Genomic Analyses ◽  
Modified Peptides ◽  
In Silico Analyses

Ribosomally synthesized and post-translationally modified peptides (RiPPs) are a structurally diverse group of natural products. They feature a wide range of intriguing posttranslational modifications as exemplified by the biarylitides. These are a family of cyclic tripeptides found in Planomonospora, carrying a biaryl-linkage between two aromatic amino acids. Recent genomic analyses revealed the minimal biosynthetic prerequisite of biarylitide biosynthesis consisting of only one ribosomally synthesized pentapeptide precursor as substrate and a modifying cytochrome P450 dependent enzyme. In silico analyses revealed that the minimal biarylitide RiPP clusters are widespread among natural product producers across phylogenetic borders including myxobacteria. We report here the genome-guided discovery of the first myxobacterial biarylitide MeYLH termed Myxarylin from Pyxidicoccus fallax An d48. Myxarylin was found to be an N-methylated tripeptide surprisingly exhibiting a C–N biaryl crosslink. In contrast to Myxarylin, previously isolated biarylitides are N-acetylated tripeptides featuring a C–C biaryl crosslink. Furthermore, the formation of Myxarylin was confirmed by heterologous expression of the identified biosynthetic genes in Myxococcus xanthus DK1622. These findings expand the structural and biosynthetic scope of biarylitide type RiPPs and emphasize the distinct biochemistry found in the myxobacterial realm.

Synthetic applications of monofluoromethylsulfonium salts

Synthesis ◽  
2021 ◽  
Author(s):  
Renate Melngaile ◽  
Janis Veliks
Keyword(s):  
Direct Synthesis ◽  
Simple Approach ◽  
Sulfonium Salts ◽  
Wide Range ◽  
Synthetic Equivalent ◽  
Synthetic Application

Monofluoromethylsulfonium salts are emerging reagents for the fluoromethylation and fluoromethylenation or fluorometyhlene transfer. This type of reagents display simple approach for introduction of fluoromethyl group into wide range of nucleophiles upon mild basic conditions. Recently, fluoromethylsulfonium salts have been demonstrated to act as a synthetic equivalent of otherwise challenging fluoromethylene synthon. For instance, these reagents can be used for the direct synthesis of monofluoroepoxides and fluorocyclopropanes from activated alkenes via sulfur fluoromethylide intermediate. Sulfonium salts are an alternative, easy-to-handle option to volatile and environmentally concerning freons for achieving monofluorinated compounds. This review focuses on synthetic application of these reagents known to date.

Recent developments in arylation of N-nucleophiles via Chan-Lam reaction: updates from 2012 onwards

2021 ◽  
Vol 17 ◽  
Author(s):  
Fahimeh Abedinifar ◽  
Mohammad Mahdavi ◽  
Elham babazadeh Rezaei ◽  
Mehdi Asadi ◽  
Bagher Larijani
Keyword(s):  
Organic Synthesis ◽  
Room Temperature ◽  
Cross Coupling ◽  
Recent Decade ◽  
Boronic Acids ◽  
Research Progress ◽  
Wide Range ◽  
Recent Developments ◽  
Comprehensive Survey ◽  
First Time

: ''Chan-Evans-Lam'' (CEL) reaction is the copper-mediated cross-coupling of N-nucleophiles with boronic acids that was independently reported in 1998 by Chan, Evans, and Lam for the first time. This reaction is accomplished at room temperature with a remarkably wide range of nucleophiles. In the recent decade, it has been particularly attractive as a convenient method for constructing the various C–N bonds in organic synthesis. Therefore, a comprehensive survey through all reported process was crucial. In this review, we summarized research progress about N-Arylation, based on the type of N-nucleophile involved in this reaction and catalysts from 2012 onwards.

scholarly journals Efficient Access to 3,5-Disubstituted 7-(Trifluoromethyl)pyrazolo[1,5-a]pyrimidines Involving SNAr and Suzuki Cross-Coupling Reactions

Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2062 ◽  
Author(s):  
Badr Jismy ◽  
Abdellatif Tikad ◽  
Mohamed Akssira ◽  
Gérald Guillaumet ◽  
Mohamed Abarbri
Keyword(s):  
Kinase Inhibitors ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Starting Material ◽  
Coupling Reactions ◽  
Synthetic Methodology ◽  
Type Reaction ◽  
Cross Coupling Reactions ◽  
Pim1 Kinase ◽  
Efficient Access

An efficient and original synthesis of various 3,5-disubstituted 7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidines is reported. A library of compounds diversely substituted in C-3 and C-5 positions was easily prepared from a common starting material, 3-bromo-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-one. In C-5 position, a SNAr type reaction was achieved by first activating the C–O bond of the lactam function with PyBroP (Bromotripyrrolidinophosphonium hexafluorophosphate), followed by the addition of amine or thiol giving monosubstituted derivatives, whereas in C-3 position, arylation was performed via Suzuki–Miyaura cross-coupling using the commercially available aromatic and heteroaromatic boronic acids. Moreover, trifluoromethylated analogues of potent Pim1 kinase inhibitors were designed following our concise synthetic methodology.

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