23654-93-5Relevant academic research and scientific papers
Metal-free visible-light-promoted C(sp3)-H functionalization of aliphatic cyclic ethers using trace O2
Blackburn, Bryan G.,Cooke, Maria Victoria,Laulhé, Sébastien,Niu, Ben,Sachidanandan, Krishnakumar
supporting information, p. 9454 - 9459 (2021/12/09)
Presented is a light-promoted C-C bond forming reaction yielding sulfone and phosphate derivatives at room temperature in the absence of metals or photoredox catalyst. This transformation proceeds in neat conditions through an auto-oxidation mechanism which is maintained through the leaching of trace amounts of O2 as sole green oxidant. This journal is
Diastereoselective Monofluorocyclopropanation Using Fluoromethylsulfonium Salts
Melngaile, Renate,Sperga, Arturs,Baldridge, Kim K.,Veliks, Janis
supporting information, p. 7174 - 7178 (2019/09/12)
Diarylfluoromethylsulfonium salts, alternatives to freons or advanced fluorinated building blocks, are bench stable and easy-to-use sources of direct fluoromethylene (:CHF) transfer to alkenes. These salts enabled development of a trans-selective monofluorinated Johnson-Corey-Chaykovsky reaction with vinyl sulfones or vinyl sulfonamides to access synthetically challenging monofluorocyclopropane scaffolds. The described method offers rapid access to monofluorinated cyclopropane building blocks with further functionalization opportunities to deliver more complex synthetic targets diastereoselectively.
Safe and Metal-Free Synthesis of 1-Alkenyl Aryl Sulfides and Their Sulfones from Thiiranes and Diaryliodonium Salts
Dong, Jun,Xu, Jiaxi
, p. 2407 - 2415 (2018/04/16)
A series of 1-alkenyl aryl sulfides was synthesized from thiiranes and diaryliodonium salts in tetrahydrofuran in the presence of potassium tert -butoxide. The proposed reaction mechanism involves generation of benzynes from the diaryliodonium salts in the presence of the base. Then, nucleophilic attack of the benzynes by thiiranes, followed by hydrogen abstraction and ring opening of the generated thiiranium intermediates, provides the sulfides. These sulfides were further oxidized with performic acid to the corresponding sulfones. The current method provides a metal-free and safe method for the preparation of 1-alkenyl aryl sulfides and their sulfones.
Copper(I)-catalyzed enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
Llamas, Tomas,Arrayas, Ramon Gomez,Carretero, Juan Carlos
, p. 950 - 956 (2008/01/06)
The combination of copper(I)-Taniaphos (5 mol%) is an efficient Lewis acid catalyst for the promotion of the asymmetric 1,3-dipolar cycloaddition of azomethine ylides to aryl vinyl sulfones, providing 3-sulfonylpyrrolidines in good yields and with nearly
Catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides with vinyl sulfones
Llamas, Tomas,Arrayas, Ramon Gomez,Carretero, Juan C.
, p. 1795 - 1798 (2007/10/03)
A general protocol for the enantioselective catalytic 1,3-dipolar cycloaddition of azomethine ylides with aryl vinyl sulfones is described. Nearly complete exo selectivity and enantioselectivities up to 85% ee are attained with Cu(CH3CN)4
