28691-72-7Relevant articles and documents
Copper-catalyzed Regioselective Hydroaminations of Allylic Sulfones With Aromatic Amines
Kim, Kundo,Cho, Soohong,Park, Subin,Lee, Yunmi
, p. 699 - 708 (2021)
The highly regioselective copper-catalyzed hydroaminations of terminal or γ-substituted allylic sulfones with aromatic amines is described. The combination of an N-heterocyclic carbene-copper complex and KOt-Bu plays an important role in promoting selective amination under mild reaction conditions. This catalytic reaction tolerates a wide range of functional groups and enables the efficient syntheses of new and versatile functionalized β-amino sulfones in high yields (up to 98%) with >98% regioselectivity.
Synthesis, structure, and stability of cyclopentadienyl(triphenylphosphine)(α-benzenesulfonylalkyl)nickel complexes
Julia, M.,Lauron, H.,Verpeaux, J. N.,Jeannin, Y.,Bois, C.
, p. C11 - C16 (1988)
The title complexes have been prepared in moderate yields by reaction of α-sulfonyl carbanions with Cp(PPh3)NiCl; the crystal structure of two of these complexes shows that the nickel atom is linked to the α-carbon of the sulfonyl group and there is no interaction between the metal and the SO2 moiety.When their solution in benzene are warmed to 90 deg C, these complexes very cleanly yield the corresponding α,β-unsaturated sulfone (E isomer).An efficient method of dehydrogenating secondary alkyl sulfones is reported.
Highly efficient, catalytic bis addition reactions of allyl phenyl sulfone to vinyl sulfones
Felton, Greg A.N.,Bauld, Nathan L.
, p. 4841 - 4845 (2004)
Highly efficient, electrocatalytic additions of allyl phenyl sulfone to a variety of vinyl sulfones have been accomplished. The additions are catalyzed by electrogenerated bases derived from the reactant itself, and furnish 90-94% yields of highly polar molecules in which 1mol of allyl phenyl sulfone has added consecutively, selectively, and in a linear addition mode to 2mol of the vinyl sulfone. Essentially no products are observed which incorporate other than 2mol of the vinyl sulfone. An addition to a difunctional alkene, divinylsulfone, yields a novel cyclization product, albeit in more moderate yield (41%). The use of tetraalkylammonium salts, as opposed to lithium salts, as electrolytes has been found to provide electrogenerated bases of especially high reactivity.
Gram-scale synthesis of β-sulfonyl styrenes
Chang, Meng-Yang,Wu, Yan-Shin,Hsiao, Yu-Ting
, p. 4651 - 4658 (2019/02/01)
A simple and gram-scale synthesis of β-sulfonyl styrenes has been developed starting from one-pot PPA (polyphosphoric acid)-catalyzed 1,1-diacetoxylation of arylacetaldehydes (ArCH2CHO) with acetic anhydride (Ac2O) followed by deacetoxylative sulfonylation of the resulting 1,1-diacetate intermediate with sodium sulfinates (RSO2Na) in good yields under solvent-free conditions.
Catalytic amide-mediated methyl transfer from silanes to alkenes in Fujiwara-Moritani oxidative coupling
Rauf, Waqar,Brown, John M.
supporting information; experimental part, p. 4228 - 4230 (2009/03/12)
(Chemical Equation Presented) Intramolecular assistance: Carbon-bound trimethylsilyl groups are activated intramolecularly by a carbonyl group and can participate in Heck reactions under oxidative conditions. Good stereoselectivities are obtained for a range of di-and trisubstituted alkenes (see example).
Enantioselective synthesis of chiral sulfones by Rh-catalyzed asymmetric addition of boronic acids to α,β-unsaturated 2-pyridyl sulfones
Mauleon, Pablo,Alonso, Ines,Rivero, Marta Rodriguez,Carretero, Juan C.
, p. 9924 - 9935 (2008/03/28)
(Chemical Equation Presented) A general and efficient method for the rhodium-catalyzed enantioselective catalytic conjugate addition of organoboronic acids to α,β-unsaturated sulfones is described. The success of the process relies on the use of α,β-unsat
An economical and convenient synthesis of vinyl sulfones
Guan, Zheng-Hui,Zuo, Wei,Zhao, Lian-Biao,Ren, Zhi-Hui,Liang, Yong-Min
, p. 1465 - 1470 (2008/02/05)
A general process for the efficient synthesis of vinyl sulfones has been developed using commercially available sulfinic acid sodium salts and dibromides. A variety of phenyl and methyl vinyl sulfones have been formed in good yields, in the absence of any catalyst. Georg Thieme Verlag Stuttgart.
[Pd(Ar-BIAN)(alkene)]-catalyzed highly chemo-, regio-, and stereoselective semihydrogenation of 1,2-allenyl phosphonates and related compounds
Guo, Hao,Zheng, Zilong,Yu, Fei,Ma, Shengming,Holuigue, Alexandre,Tromp, Dorette S.,Elsevier, Cornelis J.,Yu, Yihua
, p. 4997 - 5000 (2007/10/03)
(Chemical Equation Presented) Often elusive, trisubstituted (Z)-1-alkenyl phosphonates can be prepared by the semihydrogenation of allenyl phosphonates in the presence of Pd complex 1. This reaction, which occurs in high yield with high chemo-, regio-, an
Facile method for solid-phase synthesis of vinyl sulfones using polystyrene-supported selenomethyl aryl sulfone
Sheng, Shou-Ri,Zhou, Wei,Zhong, Ming-Hua,Liu, Xiao-Ling,Chen, Hui-Zong
, p. 815 - 821 (2007/10/03)
Treatment of novel polystyrene-supported selenomethyl aryl sulfone with LDA followed by alkylation and oxidation elimination efficiently afforded vinyl sulfones in good yields and purities.
Polystyrene-Supported α-Seleno Carbanions: Efficient Reagents for Highly Stereocontrolled Syntheses of Vinylphosphonates and Vinylsulfones
Xu, Wei Ming,Tang, E,Huang, Xian
, p. 2094 - 2098 (2007/10/03)
Polystyrene-supported selenomethyl-phosphonate and polystyrene-supported selenomethyl-sulfonates have been prepared. These novel reagents were treated with LDA (or n-BuLi) to produce polystyrene-supported α-seleno carbanions, which reacted with alkyl halides, followed by stereospecific selenoxide syn-elimination to give E-vinylphosphonates and E-vinylsulfones respectively. And also these novel polymer reagents can be regenerated and reused.