1260149-67-4Relevant academic research and scientific papers
Photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sulfinates
Mulina, Olga M.,Ilovaisky, Alexey I.,Opatz, Till,Terent'ev, Alexander O.
, (2021)
A metal-free visible light photoredox-catalyzed synthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates in moderate to high yields is described. The reaction proceeds in ethanol and uses eosin Y as a readily available photocatalyst in combination with nitrobenzene as an electron shuttle. Taking into account the number of steps involved (generation of the sulfonyl radical, its addition to the double bond, elimination of molecular nitrogen with formation of an iminyl radical, followed by its reduction and protonation) as well as the number of redox-active reaction partners involved, the selectivity of the process is quite impressive.
Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I
Mulina, Olga M.,Doronin, Mikhail M.,Terent'ev, Alexander O.
, (2021/10/16)
A wide range of N-unsubstituted enaminosulfones were obtained via electrochemical sulfonylation of vinyl azides with sulfonyl radicals generated from sodium sulfinates. The discovery of N-unsubstituted enaminosulfones synthesis is based on a unique ability of the azido group to eliminate the N2 molecule. The process is performed under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode applying NH4I both as the redox catalyst and the supporting electrolyte.
Electrochemically Induced Synthesis of Sulfonylated N-Unsubstituted Enamines from Vinyl Azides and Sulfonyl Hydrazides
Mulina, Olga M.,Zhironkina, Nataliya V.,Paveliev, Stanislav A.,Demchuk, Dmitry V.,Terent'Ev, Alexander O.
, p. 1818 - 1824 (2020/03/04)
Sulfonylated N-unsubstituted enamines were synthesized through a chain of chemical and electrochemical transformations via sulfonylation of vinyl azides. The disclosing of the N-unsubstituted enamines synthesis was based on a unique property of the azido group, which is its ability to eliminate the N2 molecule. Furthermore, a formal paradox is observed: A double bond reacts and a double bond is retained. Electrosynthesis proceeded in an undivided cell equipped with a graphite anode and a stainless steel cathode; NH4I was used as a supporting electrolyte.
Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylosulfones: A practical approach to chiral β-amido sulfones
Jiang, Jun,Wang, Yan,Zhang, Xumu
, p. 1570 - 1573 (2014/05/20)
The efficient and highly enantioselective catalytic asymmetric hydrogenation of β-acetylamino acrylosulfone has been achieved by employing Rhodium-TangPhos as catalyst. A series of β-amido sulfone products are obtained with excellent yields and good enantioselectivities.
Rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/ arylsulfonyl)acetonitriles: Efficient synthesis of (Z)-β- sulfonylvinylamines and β-Keto sulfones
Tsui, Gavin Chit,Glenadel, Quentin,Lau, Chan,Lautens, Mark
scheme or table, p. 208 - 211 (2011/03/19)
An efficient rhodium(I)-catalyzed addition of arylboronic acids to (benzyl-/arylsulfonyl)acetonitrile is described. Novel β-sulfonylvinylamine products are formed in a stereoselective fashion (Z-alkene). Upon hydrolysis, useful β-keto sulfones are obtained with a broad scope of aryl and sulfonyl substituents.
Synthesis of unsymmetrical polysubstituted pyridines from β-sulfonylvinylamines via 1-aza-allyl anion intermediates
Lau, Chan,Tsui, Gavin Chit,Lautens, Mark
supporting information; experimental part, p. 3908 - 3914 (2012/01/11)
A modular synthesis of highly functionalized unsymmetrical pyridines has been developed from reacting β-sulfonylvinylamines with α,β-unsaturated systems in the presence of base via the formation of 1-aza-allyl anion intermediates. Georg Thieme Verlag Stut
