2525-55-5Relevant academic research and scientific papers
A novel synthesis of (β-organochalcogenyl)allyl phenyl sulfoxides via regioselective hydrochalcogenation reaction of 1,2-allenyl sulfoxides
Wu, Zhimeng,Shen, Ruwei,Ren, Lianjun,Huang, Xian
, p. 2171 - 2175 (2005)
(β-Organochalcogenyl)allyl phenyl sulfoxides 2 were prepared by treatment of allenyl sulfoxides 1 with sodium organyl chalcogenolates in good yields. The reaction was regioselective, giving exclusively one isomer in all cases. The applications of (β-pheny
Twofold Radical-Based Synthesis of N, C-Difunctionalized Bicyclo[1.1.1]pentanes
Anderson, Edward A.,Mousseau, James. J.,Nugent, Jeremy,Owen, Benjamin,Pickford, Helena D.,Smith, Russell C.
supporting information, p. 9729 - 9736 (2021/07/19)
Bicyclo[1.1.1]pentylamines (BCPAs) are of growing importance to the pharmaceutical industry as sp3-rich bioisosteres of anilines and N-tert-butyl groups. Here we report a facile synthesis of 1,3-disubstituted BCPAs using a twofold radical functionalization strategy. Sulfonamidyl radicals, generated through fragmentation of α-iodoaziridines, undergo initial addition to [1.1.1]propellane to afford iodo-BCPAs; the newly formed C-I bond in these products is then functionalized via a silyl-mediated Giese reaction. This chemistry also translates smoothly to 1,3-disubstituted iodo-BCPs. A wide variety of radical acceptors and iodo-BCPAs are accommodated, providing straightforward access to an array of valuable aniline-like isosteres.
Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin-Mediated Photoredox Catalysis
Ramirez, Nieves P.,Lana-Villarreal, Teresa,Gonzalez-Gomez, Jose C.
, p. 1539 - 1550 (2019/08/07)
We describe herein a direct decarboxylative allylation of aliphatic carboxylic acids with allylsulfones using visible light and riboflavin tetraacetate (RFTA) as photocatalyst. The reaction proceeds at room temperature tolerating a wide range of functiona
Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines
Martzel, Thomas,Lohier, Jean-Fran?ois,Gaumont, Annie-Claude,Brière, Jean-Fran?ois,Perrio, Stéphane
, p. 5069 - 5073 (2018/09/14)
An operationally simple methodology for the synthesis of 4-sulfonyl-3-pyrrolines is described using a propargylic sulfone and N-sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof-of-concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase-transfer catalysts.
Aryl Ketone Catalyzed Radical Allylation of C(sp3)-H Bonds under Photoirradiation
Kamijo, Shin,Kamijo, Kaori,Maruoka, Kiyotaka,Murafuji, Toshihiro
, p. 6516 - 6519 (2016/12/23)
The catalytic introduction of an allyl group at nonacidic C(sp3)-H bonds was achieved under photoirradiation, in which 1,2-bis(phenylsulfonyl)-2-propene acts as an allyl source and 5,7,12,14-pentacenetetrone (PT) works as a C-H bond-cleaving catalyst. A variety of substances, including alkanes, carbamates, ethers, sulfides, and alcohols, were chemoselectively allylated in a single step under neutral conditions. The present transformation is catalyzed solely by an organic molecule, PT, and proceeds smoothly even under visible light irradiation (425 nm) in the case of alkanes as a starting substance.
Reactions of propargylic bromides with sodium sulfinates
Chang, Meng-Yang,Wu, Ming-Hao
supporting information, p. 411 - 416 (2014/03/21)
A one-pot, palladium-catalyzed synthesis of substituted 2,3-bissulfonylpropenes starting with propargylic bromides and sodium sulfinates (RSO2Na) in the presence of n-Bu4NF under refluxing aqueous 1,4-dioxane conditions for eight hours in moderate yields is described. Georg Thieme Verlag Stuttgart. New York.
Use of 2,3-Bis(phenylsulfonyl)-1-propene as a Multicoupling Reagent
Padwa, Albert,Kline, Donald N.,Murphree, S. Shaun,Yeske, Philip E.
, p. 298 - 306 (2007/10/02)
2,3-Bis(phenylsulfonyl)-1-propene (1) reacts with various amines to afford products derived from addition across the double bond as well as SN2' displacement.When treated with 2-piperidinemethanol, bissulfone 1 gave the expected SN2'
USE OF 2,3-(DIPHENYLSULFONYL)-1-PROPENE AS AN ALLENE EQUIVALENT IN CYCLOADDITION CHEMISTRY
Padwa, Albert,Kline, Donald N.,Norman, Bryan H.
, p. 265 - 268 (2007/10/02)
The cycloaddition chemistry of 2,3-(diphenylsulfonyl)-1-propene with several nitrones has been investigated.The reagent formally corresponds to an allene equivalent.
1,3-Dipolar Cycloadditions with Alkynyl Phenyl Sulphones
Croce, Piero Dalla,Rosa, Concetta La,Zecchi, Gaetano
, p. 2621 - 2624 (2007/10/02)
Alkynyl phenyl sulphones (4) react with the nitrile oxide (1), the nitrile imine (2), and sydnone (3) to afford predominantly or exclusively 4-phenylsulphonyl substituted cycloadducts (5), (7), and (9).The observed regioselectivity is discussed.
