N-Tosyl-S-difluoromethyl-S-phenylsulfoximine: a new difluoromethylation reagent for S-, N-, and C-nucleophiles.
نویسندگان
چکیده
The first alpha-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(II)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF(2)H group to S-, N-, and C-nucleophiles. Deuterium-labeling experiments suggest that a difluorocarbene mechanism is involved in the current difluoromethylation reactions.
منابع مشابه
Efficient Difluoromethylation of sp3 Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic Bases
Introduction of a difluoromethyl (CF2H) unit into organic molecules is of specific interest in medicinal chemistry and chemical biology, as compounds with a CF2H moiety can act as an isostere to molecules having a methanol (CH2OH) unit with improved lipophilicity. Among several strategies for the synthesis of CF2H compounds available, a late-stage difluoromethylation using easy-to-handle reagen...
متن کاملOxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H‐Containing Alcohols
We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF2 H) group into alkenes by visible-light-driven photoredox catalysis. The use of fac-[Ir(ppy)3] (ppy=2-pyridylphenyl) photocatalyst and shelf-stable Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, as a CF2 H source is the key to success. The well-designed photoredox system achieves synt...
متن کاملHighly stereoselective synthesis of monofluoroalkenes from alpha-fluorosulfoximines and nitrones.
between the charge distribution of the amide bond and the fluoroalkene moiety, as well as their dipole moments. Therefore, a monofluoroalkene moiety can be used as a peptidomimetic unit in the design of protease inhibitors; this type of rigid isostere of the peptidic bond can facilitate the cis/ trans conformational control of the replaced peptidic fragment. Numerous synthetic endeavors have be...
متن کاملMetal-free di- and tri-fluoromethylation of alkenes realized by visible-light-induced perylene photoredox catalysis.
Regioselective amino-difluoromethylation of aromatic alkenes via C(sp3)-CF2H and C(sp3)-N bond formation with the C 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0000000000000000000000000000000000 0...
متن کاملParasites of some bonyfish species from the Boojagh wetland in the southwest shores of the Caspian Sea
The Boojagh international wetland with a surface area of 80 hectares and 25 fish species is located in the southwest shores of the Caspian Sea (Guilan province, Iran), but there is no report about fish parasites in this wetland. In the present study, a total of 553 individuals of 8 fish species including Cyprinus carpio (n=71), Abramis bjoerkna (n=153), Carassius auratus gibelio (n=89), Esox...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic letters
دوره 11 10 شماره
صفحات -
تاریخ انتشار 2009