28525-02-2Relevant academic research and scientific papers
Aryne 1,2,3,5-Tetrasubstitution Enabled by 3-Silylaryne and Allyl Sulfoxide via an Aromatic 1,3-Silyl Migration
Shi, Jiarong,Li, Lianggui,Shan, Chunhui,Wang, Junli,Chen, Zhonghong,Gu, Rongrong,He, Jia,Tan, Min,Lan, Yu,Li, Yang
supporting information, p. 2178 - 2184 (2021/02/16)
Although benzyne has been well-known to serve as a synthon that can conveniently prepare various 1,2-difunctionalized benzenes, the sites other than its formal triple bond remain silent in typical benzyne transformations. An unprecedented aryne 1,2,3,5-tetrasubstitution was realized from 3-silylbenzyne and aryl allyl sulfoxide, the mechanistic pathway of which includes a regioselective aryne insertion into the SO bond, a [3,6]-sigmatropic rearrangement, and a thermal aromatic 1,3-silyl migration cascade.
Sulfoxide synthesis from sulfinate esters under Pummerer-like conditions
Kobayashi, Akihiro,Matsuzawa, Tsubasa,Hosoya, Takamitsu,Yoshida, Suguru
supporting information, p. 5429 - 5432 (2020/06/04)
A facile synthetic method for the preparation of allyl sulfoxides byS-allylation of sulfinate esters proceeds through sulfonium intermediates without [3,3]-sigmatropic rearrangement and further Pummerer-type reactions of the resulting allyl sulfoxides. On the basis of the plausible reaction mechanism involving sulfonium salt intermediates,S-alkynylation andS-arylation were also accomplished.
Aryne 1,2,3-Trifunctionalization with Aryl Allyl Sulfoxides
Li, Yuanyuan,Qiu, Dachuan,Gu, Rongrong,Wang, Junli,Shi, Jiarong,Li, Yang
supporting information, p. 10814 - 10817 (2016/09/12)
An aryne 1,2,3-trisubstitution with aryl allyl sulfoxides is accomplished, featuring an incorporation of C-S, C-O, and C-C bonds on the consecutive positions of a benzene ring. The reaction condition is mild with broad substrate scope. Preliminary mechani
VO2F(dmpz)2: A new catalyst for selective oxidation of organic sulfides to sulfoxides with H2O2
Hussain, Sahid,Talukdar, Dhrubajyoti,Chaudhuri, Mihir K.,Bharadwaj, Saitanya K.
, p. 6512 - 6515,4 (2012/12/11)
A newly developed and structurally characterized vanadium complex [VO 2F(dmpz)2] (dmpz = 3, 5 dimethyl pyrazole) is reported as recyclable catalyst for the selective oxidation of organic sulfides with H 2O2 in C
Copper catalyzed oxidation of sulfides to sulfoxides with aqueous hydrogen peroxide
Velusamy, Subbarayan,Kumar, Akkilagunta V.,Saini, Rakesh,Punniyamurthy
, p. 3819 - 3822 (2007/10/03)
Copper(II) complex 1 catalyzes the oxidation of sulfides to sulfoxides with 30% H2O2 in high yields. Addition of a catalytic amount of TEMPO to the reaction mixture enhances the conversion and selectivity. Complex 1 can be recycled without loss of activity.
Iodic acid (HIO3) in combination with tetraethylammonium bromide as a catalyst for selective and accelerated sulfoxidation
Salgaonkar, Paresh D.,Shukla, Vidyanand G.,Akamanchi
, p. 2805 - 2810 (2007/10/03)
The article describes the use of iodic acid in combination with catalytic amounts of tetraethylammonium bromide (TEAB) as a mild and alternative reagent system for oxidation of sulfides to sulfoxides. The salient features of the developed system are room-
MECHANISM OF TELOMERIZATION OF 1,3-DIENES WITH SULFINIC ACIDS, CATALYZED BY PALLADIUM COMPLEXES
Dzhemilev, U. M.,Kunakova, R. V.,Gaisin, R. L.,Valyamova, F. G.,Tolstikov, G. A.
, p. 1030 - 1033 (2007/10/02)
The probable telomerization mechanism was studied by IR spectroscopy, according to which the reaction of 1,3-dienes with sulfinic acids proceeds through a stage of formation of S-sulfinate complexes of palladium, which bring about the formation of molecules of unsaturated sulfones.
STRUCTURAL EFFECTS UPON COMPETITIVE DECOMPOSITION PATHWAYS OF THIOSULFOXIDE INTERMEDIATES
Baechler, Raymond D.,Filippo, Lynn James San,Schroll, Alayne
, p. 5247 - 5250 (2007/10/02)
Mixtures of sulfides and disulfides are obtained upon reaction of boron trisulfide with a series of allyl aryl sulfoxides, with the product distributions dependent upon the structures of the intermediate thiosulfoxides.
Asymmetric Induction in the Additions of Anions of Allylic Sulfoxides to Benzaldehyde
Antonjuk, David J.,Ridley, Damon D.,Smal, Mary A.
, p. 2635 - 2651 (2007/10/02)
Addition reactions of anions of aryl allyl sulfoxides to benzaldehyde proceed readily in moderate yields and afford mixtures of products resulting from α- and γ-attack on the allyl anion.The γ-products all possess the (E)-configuration around the double bond, and asymmetric induction occurs in the addition to the extent that the major/minor diastereomer ratio exceeds 2:1, generally.Electronic factors are believed to be responsible for this "remote" asymmetric induction.Mixtures of all four possible diastereomers are observed in the products from α-attack and evidence is presented which suggests that the ratios of these products are as a result of epimerization of two of the chiral centres by sigmatropic rearrangement.
