98181-84-1Relevant academic research and scientific papers
Photoredox-Catalyzed Intramolecular Difluoromethylation of N-Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H-Containing 2-Azaspiro[4.5]deca-6,9-diene-3,8-diones
Zhang, Zuxiao,Tang, Xiao-Jun,Dolbier, William R.
supporting information, p. 1048 - 1051 (2016/03/15)
A visible light-mediated difluoromethylation of N-benzylacrylamides with HCF2SO2Cl as the HCF2 radical precursor is described. The reaction incorporates a tandem cyclization/dearomatization process to afford various difluoromethylated 2-azaspiro[4.5]deca-6,9-diene-3,8-diones bearing adjacent quaternary stereocenters under mild conditions in moderate to excellent yields.
Efficient cu-catalyzed atom transfer radical addition reactions of fluoroalkylsulfonyl chlorides with electron-deficient alkenes induced by visible light
Tang, Xiao-Jun,Dolbier, William R.
supporting information, p. 4246 - 4249 (2015/04/14)
Fluoroalkylsulfonyl chlorides, RfSO2Cl, in which Rf=CF3, C4F9, CF2H, CH2F, and CH2CF3, are used as a source of fluorinated radicals to add fluoroalkyl groups to electron-deficient, unsaturated carbonyl compounds. Photochemical conditions, using Cu mediation, are used to produce the respective α-chloro-β-fluoroalkylcarbonyl products in excellent yields through an atom transfer radical addition (ATRA) process. Facile nucleophilic replacement of the α-chloro substituent is shown to lead to further diverse functionalization of the products.
Photoredox-catalyzed tandem radical cyclization of N-arylacrylamides: General methods to construct fluorinated 3,3-disubstituted 2-oxindoles using fluoroalkylsulfonyl chlorides
Tang, Xiao-Jun,Thomoson, Charles S.,Dolbier, William R.
supporting information, p. 4594 - 4597 (2015/01/08)
Fluorinated radicals were generated from RfSO2Cl by photoredox catalysis under mild conditions, where Rf = n-C4F9, CF3, CF2H, CH2F, CH2CF3, and CF2CO2Me. This method provided a general way to construct fluorinated 2-oxindoles from reaction with N-arylacrylamides via a proposed tandem radical cyclization process.
Reactions of Halogenated Methanesulfonyl Chlorides with Trimethylamine and an Inverse Sulfene-Amine Adduct
Rheude, Udo,Sundermeyer, Wolfgang
, p. 2208 - 2219 (2007/10/02)
Starting from chlorofluoromethane (3), prepared by a convenient procedure, fluoromethanesulfonyl chloride (6) was synthesized easily and cleanly via the intermediate thioethers 4-chlorobenzyl fluoromethyl sulfide (4) or benzhydryl fluoromethyl sulfide (5) for the first time.Reaction of 6 with trimethylamine leads to an inverse amine-adduct 9a of fluorosulfene, which was characterized by transformation to (fluoromethyl)trimethylammonium chloride (10) and by oxidation to the sulfonate 11.The structure of 9a is discussed on the basis of spectroscopic data.Bromomethanesulfonyl chloride (17) similarly as chloromethanesulfonyl chloride leads to a dimeric adduct 18a of (bromomethylsulfonyl)sulfene and trimethylamine, which is characterized by its hydrolysis product 19a. 2,4-Dibromo-1,3-dithietane 1,1,3,3-tetraoxide (15) could not be detected, but has been prepared by another method.The products, resulting from the monohalogenmethanesulfonyl chlorides, can be explained by the intermediate existence of the monohalogensulfenes.Difluoro- (20) and dichloromethanesulfonyl chloride (24) gave no sulfeneamine adducts; 20 yields (difluoromethyl)trimethylammonium chloride and other products while from 24 under various conditions only trimethylammonium trichloromethanesulfinate (25) is formed.
