850720-97-7

Upstream product

• 14367-98-7 1-(2-fluorophenyl)-2-nitroethan-1-one 
• 21849-40-1 dibromamine-T 
• 446-52-6 2-Fluorobenzaldehyde 
• 92755-81-2 N-bromo-p-toluenesulfonamide 
• 393-52-2 2-Fluorobenzoyl chloride 
• 445-29-4 o-fluoro-benzoic acid 
• 941-55-9 4-toluenesulfonyl azide 
• 70-55-3 toluene-4-sulfonamide 
• 127-65-1 chloroamine-T 

Downstream Products

• 1043425-48-4 C₁₄H₁₁ClFNO₂S 
• 1356832-76-2 3-ethoxycarbonyl-3-ethoxycarbonylmethyl-7-fluoro-2-tosylisoindolin-1-one 
• 1918125-85-5 (4R,5R)-2-(2-(diphenylphosphaneyl)phenyl)-4,5-diphenyl-4,5-dihydrooxazole 
• 1202793-05-2 (4R,5R)-2-(2-fluorophenyl)-4,5-dihydro-4,5-diphenyloxazole 
• 285565-39-1 4-methyl-N-(1-phenylbut-3-yn-1-yl)benzenesulfonamide 
• 24517-59-7 2-phenyl-1-(4-methylbenzenesulfonyl)pyrrolidine 

Relevant academic research and scientific papers

Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols

We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is

Stereospecific Synthesis of cis-2,5-Disubstituted Pyrrolidines via N, O-Acetals Formed by Hydroamination Cyclization-Hydroalkoxylation of Homopropargylic Sulfonamides in HFIP

We reported a novel two-step stereoselective synthesis of functionalized pyrrolidines from homopropargylic sulfonamides and nucleophiles via an isolable N,O-acetal intermediates. This reaction features mild conditions and good scope of substrates. In addition, the use of hexafluoroisopropanol, acting as a solvent, an additive, a weak nucleophile, and a good leaving group, is pivotal to the success of the method. Moreover, reactions of chiral homopropargylic sulfonamides afford only 2,5-cis-disubstituted pyrrolidines with high diastereoselectivity (up to >99:1 dr) and enantioselectivity (up to >99% ee). The overall reaction constitutes a formal 1,1-bifunctionalization of terminal alkynes, which has hitherto been reported only rarely. Additionally, this method provides efficient access to pharmaceutical intermediate and to carry out postmodification of natural products.

Controllable construction of isoquinolinedione and isocoumarin scaffolds: Via RhIII-catalyzed C-H annulation of N -tosylbenzamides with diazo compounds

A highly efficient protocol for the synthesis of isoquinolinediones by RhIII-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.

Improvements of C-H Radio-Iodination of N-Acylsulfonamides toward Implementation in Clinics

An improved protocol to perform C-H radio-iodination is described. These new conditions allow rapid and clean formation of radio-iodinated N-acylsulfonamides using [125 I]NIS and catalytic amounts of palladium acetate and para-toluenesulfonic a

Formation of esters and amides via metal-free Csp2-Csp3 bond cleavage of α-nitro ketone: Mechanistic insight to the reaction pathway

A catalyst free protocol for hucleophilic Csp2-Csp3 bond cleavage of a-nitroketone has been achieved for the formation of C-O and C-N bond. A series of differently substituted a-nitroketones could be selectively cleaved and converted into corresponding esters and tosylamides in presence of alcohols and bromamine-T respectively. Mechanism of the C-C bond cleavage has been proposed by identifying different reaction intermediates using IR and NMR spectroscopic methods.

Co-Catalyzed Synthesis of N-Sulfonylcarboxamides from Carboxylic Acids and Sulfonyl Azides

A Co-catalyzed effective synthesis of N-sulfonylcarboxamides from the reaction of carboxylic acids and organic azides in the presence of isocyanide has been developed. The protocol has the advantages of short time, low temperature, and being oxidant-free, which provides a new and simple approach for the synthesis of N-sulfonylcarboxamides in good to excellent yields with a broad substrate scope.

Palladium-Mediated Site-Selective C-H Radio-iodination

The palladium-mediated C-H radio-iodination of arenes using sodium iodide as the primary isotopic source is reported and performed without chemical know-how in 30 min and applied to the synthesis of complex radio-iodinated compounds of biological interest.

Organocatalytic Direct N-Acylation of Amides with Aldehydes under Oxidative Conditions

The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of azolium salt C3 and an inorganic base using 3,3′,5,5′-tetra-tert-butyldiphenoquinone as the oxidant, thus providing an efficient approach for the synthesis of three types of imide compounds including N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in good yield.

Unexpected C-C bond cleavage of α-nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation

A new catalyst-free protocol for C-N bond formation via the cleavage of α-nitroketone has been developed. When α-nitroketones are treated with TsNBr2 in the presence of potassium carbonate, unexpected cleavage of C(O)-CHNO2 bond of α-nitroketone was observed followed by the formation of corresponding amide. Various nitroketones could be converted to corresponding amide using this procedure.

Room-temperature ortho-alkoxylation and -halogenation of N-tosylbenzamides by using palladium(II)-catalyzed C-H activation

The N-tosylcarboxamide group can direct the room-temperature palladium-catalyzed C-H alkoxylation and halogenation of substituted arenes in a simple and mild procedure. The room-temperature stoichiometric cyclopalladation of N-tosylbenzamide was first studied, and the ability of the palladacycle to react with oxidants to form C-X and C-O bonds under mild conditions was demonstrated. The reaction conditions were then adapted to promote room-temperature ortho-alkoxylations and ortho-halogenations of N-tosylbenzamides using palladium as catalyst. The scope and limitation of both alkoxylations and halogenations was studied and the subsequent functional transformation of the N-tosylcarboxamide group through nucleophilic additions was evaluated. This methodology offers a simple and mild route to diversely functionalized arenes.