36458-32-9

Upstream product

• 421-85-2 Trifluoromethanesulfonamide 
• 100-41-4 ethylbenzene 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 121-44-8 triethylamine 
• 618-36-0 rac-methylbenzylamine 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 10604-60-1 (1-iodoethyl)benzene 

Downstream Products

• 1159505-76-6 C₉H₈F₅NO₂S 
• 114635-89-1 C₉H₁₀F₃NO₂S 

Relevant academic research and scientific papers

Catalytic intermolecular amination of C-H bonds: Method development and mechanistic insights

Reaction methodology for intermolecular C-H amination of benzylic and 3° C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3° centers, displays high chemoselectivity for benzylic oxidation, and enables the facile preparation of isotopically enriched 15N-labeled compounds. Access to substituted amines, amino alcohols, and diamines is thereby made possible in a single transformation. Important information relevant to understanding the initial steps in the catalytic cycle, reaction chemoselectivity, the nature of the active oxidant, and pathways for catalyst inactivation has been gained through mechanistic analysis; these studies are also presented.

General, Straightforward, and Atom-Economical Synthesis of Vinyl Triflimides

Vinyl triflimides were only accessible recently and their chemistry is yet to be discovered. Herein, we describe a general, straightforward and atom-economical synthesis of these materials from alkynes and triflimide. A vast array of terminal and internal alkynes with broad spectrum of functionalities could be employed to generate various di- and trisubstituted vinyl triflimides regiospecifically with high to specific stereoselectivity. Moreover, the protocol could be conducted on gram scale using terminal and internal alkynes. Preliminarily attempts to probe the unprecedented reactivity of vinyl triflimides revealed part of its chemical properties.

Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis

The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.

PALLADIUM-CATALYZED ORTHO-FLUORINATION

A new method of ortho-fluorination where an aryl C—H bond is directly replaced by an aryl C-F bond in a palladium-catalyzed reaction is provided. The method includes the ortho-fluorination of a triflamide protected benzylamine, a palladium catalyst, such as Pd(OTf)2, a fluorinating reagent such as N-fluoro-2,4,6-trimethylpyridinium triflate, and a ligand to promote the reaction such as N-methylpyrrolidinone (NMP).

Versatile Pd(OTf)2·2H2O-catalyzed ortho-fluorination using NMP as a promoter

(Chemical Equation Presented) Pd(OTf)2·2H 2O-catalyzed ortho-fluorination of triflamide-protected benzylamines is reported. The use of N-fluoro-2,4,6-trimethylpyridinium triflate as the F+ source and NMP as a promoter is crucial for this reaction. The conversion of triflamide into a wide range of synthetically useful functional groups makes this fluorination protocol broadly applicable in medicinal chemistry and synthesis.

Convenient synthesis of primary sulfonamides

An efficient protocol for a one-pot synthesis of mono-sulfonamides has been developed. It features utilization of excess of sulfonylating agent followed by base mediated recovery of the primary sulfonamide.