scholarly journals Validation of Arylphosphorothiolates as Convergent Substrates for Ar-SF4Cl and Ar-SF5 Synthesis

Synthesis ◽  
2021 ◽  
Author(s):  
Josep Cornella ◽  
Lin Wang ◽  
Shengyang Ni
Keyword(s):  
Functional Groups ◽  
Boronic Acids ◽  
Diazonium Salts ◽  
Good Tolerance ◽  
Fluorinating Agent ◽  
Aryl Iodides

AbstractIn this manuscript we describe the oxidative fluorination of aryl phosphorothiolates to access Ar-SF4Cl compounds. These compounds serve as precursors for the highly coveted Ar-SF5 compounds. The use of phosphorothiolates as starting materials permits access to Ar-SF4Cl from a wide variety of available starting materials, namely boronic acids, diazonium salts, aryl iodides, thiophenols, or simple arenes. The protocol has been demonstrated for >10 examples and showed good tolerance to various functional groups. Finally, we demonstrated that AgBF4 can be used as a fluorinating agent, affording good yields of an Ar-SF5.

Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions

Synthesis ◽  
2021 ◽  
Author(s):  
Alexandre Desaintjean ◽  
Fanny Danton ◽  
Paul Knochel
Keyword(s):  
Exchange Reaction ◽  
Nitro Group ◽  
General Formula ◽  
Functional Groups ◽  
Exchange Reactions ◽  
Acyl Chlorides ◽  
Aryl Iodides ◽  
Highly Sensitive ◽  
Wide Range ◽  
Magnesium Exchange

A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents were prepared in toluene within 10 to 120 min between −78 °C and 25 °C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as a triazene or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arenes and alkenes derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.

scholarly journals General Synthesis of 1-Aryl-6-azaisocytosines and Their Utilization for the Preparation of Related Condensed 1,2,4-Triazines

Molecules ◽  
2019 ◽  
Vol 24 (19) ◽  
pp. 3558 ◽  
Author(s):  
František Zálešák ◽  
Jan Slouka ◽  
Jakub Stýskala
Keyword(s):  
Functional Groups ◽  
Heterocyclic Compounds ◽  
Tautomeric Equilibrium ◽  
Diazonium Salts ◽  
General Synthesis

A simple general synthesis of 1-aryl-6-azaisocytosine-5-carbonitriles 4 is described. This method is based on coupling diazonium salts with cyanoacetylcyanamide 2 and then cyclization of the formed 2-arylhydrazono-2-cyanoacetylcyanamides 3. The 6-azaisocytosines 4 were studied with respect to tautomeric equilibrium and the transformation of functional groups, and used in the synthesis of the condensed heterocyclic compounds: Purine isosteric imidazo[2,1-c]-[1,2,4]triazine 8 and the 1,2,4-triazino[2,3-a]quinazolines 9–12.

ChemInform Abstract: Chelation-Assisted Cross-Coupling of Anilines Through in situ Activation as Diazonium Salts with Boronic Acids under Ligand-, Base-, and Salt-Free Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (48) ◽  
pp. no-no
Author(s):  
Roxan Joncour ◽  
Nicolas Susperregui ◽  
Noel Pinaud ◽  
Karinne Miqueu ◽  
Eric Fouquet ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Diazonium Salts ◽  
In Situ Activation

Relativistic Functional Groups: Aryl Carbon—Gold Bond Formation by Selective Transmetalation of Boronic Acids.

ChemInform ◽  
2007 ◽  
Vol 38 (15) ◽  
Author(s):  
David V. Partyka ◽  
Matthias Zeller ◽  
Allen D. Hunter ◽  
Thomas G. Gray
Keyword(s):  
Functional Groups ◽  
Bond Formation ◽  
Boronic Acids

scholarly journals Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2412 ◽  
Author(s):  
Weijia Shi ◽  
Gang Zou
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Cross Coupling ◽  
Methyl Tert Butyl Ether ◽  
Palladium Chloride ◽  
Butyl Ether ◽  
Good Tolerance ◽  
Palladium Catalyzed ◽  
Supported Palladium

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K2CO3 in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH3 or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

scholarly journals Synthesis of Phenols via Metal-Free Hydroxylation of Aryl Boronic Acids with Aqueous TBHP

2020 ◽  
Vol 2020 ◽  
pp. 1-7 ◽  
Author(s):  
Tanveer MahmadAlli Shaikh
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Boronic Acids ◽  
Aromatic Rings ◽  
Metal Free ◽  
Alternate Procedure

An alternate procedure for oxidative hydroxylation of aryl boronic acids with aqueous TBHP to access phenols is described. The protocol tolerated various functional groups substituted with aromatic rings. The reaction was performed in water and free from transition metal oxidants.

A Green Alternative for Aryl Iodide Preparation from Aromatic Amines

2020 ◽  
Vol 17 (2) ◽  
pp. 131-135
Author(s):  
Zohreh Shahnavaz ◽  
Lia Zaharani ◽  
Mohd Rafie Johan ◽  
Nader Ghaffari Khaligh
Keyword(s):  
Low Cost ◽  
Cost Effective ◽  
Raw Material ◽  
Diazonium Salts ◽  
Separation And Purification ◽  
One Pot ◽  
Aryl Iodide ◽  
Aryl Iodides ◽  
The One

Background: In continuation of our previous work and the applications of saccharin, we encouraged to investigate the one-pot synthesis of the aryl iodides by the diazotization of the arene diazonium saccharin salts. Objective: Arene diazonium salts play an important role in organic synthesis as intermediate and a wide variety of aromatic compounds have been prepared using them. A serious drawback of arene diazonium salts is their instability in a dry state; therefore, they must be stored and handled carefully to avoid spontaneous explosion and other hazard events. Methods: The arene diazonium saccharin salts were prepared as active intermediates in situ through the reaction of various aryl amines with tert-butyl nitrite (TBN) in the presence of saccharin (Sac–H). Then, in situ obtained intermediates were used into the diazotization step without separation and purification in the current protocol. Results: A variety of aryl iodides were synthesized at a greener and low-cost method in the presence of TBN, Sac–H, glacial acetic acid, and TEAI. Conclusion: In summary, a telescopic reaction is developed for the synthesis of aryl iodides. The current methodology is safe, cost-effective, broad substrate scope, and metal-free. All used reagents are commercially available and inert to moisture and air. Also, the saccharine and tetraethylammonium cation could be partially recovered from the reaction residue, which reduces waste generation, energy consumption, raw material, and waste disposal costs.

A Universal Procedure for the [18F]Trifluoromethylation of Aryl Iodides and Aryl Boronic Acids with Highly Improved Specific Activity

2014 ◽  
Vol 53 (41) ◽  
pp. 11046-11050 ◽  
Author(s):  
Dion van der Born ◽  
Claudia Sewing ◽  
J. Koos D. M. Herscheid ◽  
Albert D. Windhorst ◽  
Romano V. A. Orru ◽  
...  
Keyword(s):  
Specific Activity ◽  
Boronic Acids ◽  
Aryl Iodides ◽  
Universal Procedure

[3+2] Cycloaddition of N-Aminopyridines and Perfluoroalkynylphosphonates: Facile Synthesis of Perfluoroalkylated Pyrazolo[1,5-a]pyridines Containing a Phosphonate Moiety

Synthesis ◽  
2018 ◽  
Vol 50 (18) ◽  
pp. 3731-3737 ◽  
Author(s):  
Hui Zhang ◽  
Weiguo Cao ◽  
Qi Huang ◽  
Dong He ◽  
Jing Han ◽  
...  
Keyword(s):  
Functional Groups ◽  
Room Temperature ◽  
Pyridine Derivatives ◽  
Facile Synthesis ◽  
Good Tolerance ◽  
Phosphonate Group ◽  
Salient Features ◽  
Operational Simplicity

1,3-Zwitterions generated from N-aminopyridines in the presence of base are trapped by perfluoroalkynylphosphonates to yield a variety of perfluoroalkylated pyrazolo[1,5-a]pyridine derivatives bearing a phosphonate group. The salient features of these [3+2] cycloadditions include operational simplicity, good tolerance of functional groups, and good to excellent yields at room temperature.

A Practical Access to Functionalized Alkyl Sulfinates

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1622-1626
Author(s):  
M. Haddad ◽  
P. Phansavath ◽  
V. Ratovelomanana-Vidal ◽  
C. Tran ◽  
B. Flamme ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cost Effective ◽  
Good Tolerance ◽  
Mild Conditions ◽  
Cost Effective Method ◽  
Wide Range

We describe herein a three-step synthesis of aliphatic sulfinates. This cost-effective method involves the use of 2-mercaptobenzothiazole under mild conditions and exhibits good yields (up to 78% over three steps). This approach provides an access to a wide range of functionalized sulfinates. A good tolerance with respect to diverse functional groups (alkene, alkyne, ether, acetal) was also noted.

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