1709-60-0Relevant academic research and scientific papers
Photoredox Catalyzed Sulfonylation of Multisubstituted Allenes with Ru(bpy)3Cl2 or Rhodamine B
Chen, Jingyun,Chen, Shufang,Jiang, Jun,Lu, Qianqian,Shi, Liyang,Xu, Zekun,Yimei, Zhao
supporting information, (2021/11/09)
A highly regio- and stereoselective sulfonylation of allenes was developed that provided direct access to α, β-substituted unsaturated sulfone. By means of visible-light photoredox catalysis, the free radicals produced by p-toluenesulfonic acid reacted with multisubstituted allenes to obtain Markovnikov-type vinyl sulfones with Ru(bpy)3Cl2 or Rhodamine B as photocatalyst. The yield of this reaction could reach up to 91%. A series of unsaturated sulfones would be used for further transformation to some valuable compounds.
tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines
Kuang, Kaimo,Wu, Meixia,Wu, Sixin,Xia, Ziqin,Xu, Qiankun,Zhang, Man,Zhou, Nengneng
supporting information, p. 3491 - 3495 (2021/06/28)
A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).
Tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the Alkynylamines and Sulfinic Acids
Qi, Zhenjie,Jiang, Yong,Wang, Yanyan,Yan, Rulong
, p. 8636 - 8644 (2018/06/18)
tert-Butyl nitrite promoted oxidative intermolecular sulfonamination of alkynes to synthesize substituted sulfonyl pyrroles from the alkynylamines and sulfinic acids via tandem addition/cyclization was developed. This reaction is performed well by employing tert-butyl nitrite as the oxidant, and various substituted sulfonyl pyrroles are formed in moderate to good yields with no requirement of metal catalysis.
Visible-Light Photocatalytic Bicyclization of 1,7-Enynes toward Functionalized Sulfone-Containing Benzo[a]fluoren-5-ones
Huang, Min-Hua,Zhu, Yi-Long,Hao, Wen-Juan,Wang, Ai-Fang,Wang, De-Cai,Liu, Feng,Wei, Ping,Tu, Shu-Jiang,Jiang, Bo
supporting information, p. 2229 - 2234 (2017/07/07)
A new visible-light photocatalytic arylsulfonylation and bicyclization of C(sp3)-tethered 1,7-enynes with sulfinic acids has been developed, delivering functionalized sulfone-containing benzo[a]fluoren-5-ones with generally good yields. This Eosin Y-catalyzed approach makes use of visible light as a safe and eco-friendly energy source to drive cascade cyclization reactions, resulting in continuous multiple bond-forming events including C–S and C–C bonds to efficiently construct polycyclic-linked alkyl aryl sulfones. (Figure presented.).
Direct Irradiaton of Aryl Sulfides: Homolytic Fragmentation and Sensitized S-Oxidation
Bonesi, Sergio M.,Crespi, Stefano,Merli, Daniele,Manet, Ilse,Albini, Angelo
, p. 9054 - 9065 (2017/09/11)
The direct irradiation of diphenyl sulfide and p-substituted thioanisoles in the presence of oxygen was investigated by means of both steady state and laser flash photolysis experiments. Two competitive pathways took place from the triplet excited state o
One-step synthesis of racemic α-amino acids from aldehydes, amine components, and gaseous CO2 by the aid of a bismetal reagent
Mita, Tsuyoshi,Higuchi, Yuki,Sato, Yoshihiro
, p. 1123 - 1128 (2013/02/23)
α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid can be divided into three basic components: an aldehyde, an amine, and carbon dioxide (CO2). We report herein that a one-step synthesis of α-amino acids has been successfully achieved from these three basic and inexpensive chemicals with a single operation, in which the mixture of an aldehyde, a sulfonamide, and gaseous CO2 was heated at 100 °C in the presence of Bu3Sn-SnBu3 and CsF. In this one-pot sequential protocol, two important intermediates (imine and α-amino stannane) are involved and the stannyl anion generated in situ plays a crucial role, particularly for the efficient stannylation of the imine in the presence of proton sources and for promoting retrostannylation of the undesired α-alkoxy stannane owing to its high stability and tolerance of the presence of proton sources. This methodology enabled the synthesis of a wide range of racemic arylglycine derivatives in high yields. Go retro! α-Amino acids are essential resources for human life and are highly useful as building blocks for organic synthesis. The core framework of an α-amino acid is retrosynthesized to an aldehyde, an amine, and carbon dioxide. A one-step synthesis of α-amin Copyright
Microwave-accelerated Pd-catalyzed desulfitative direct C2-arylation of free (NH)-indoles with arylsulfinic acids
Miao, Tao,Li, Pinhua,Wang, Guan-Wu,Wang, Lei
, p. 3185 - 3190 (2014/01/06)
The rapid and efficient direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a microwave-accelerated palladium-catalyzed desulfitation reaction. By using PdCl2 as a catalyst, silver acetate as an oxidant, and H2SO4 as an additive, arylsulfinic acids with both electron-donating and electron-withdrawing groups underwent desulfitative coupling with an array of free (NH)-indoles, thereby selectively providing C2-arylindoles in good yields. From C2 shining sea: The direct C2-arylation of free (NH)-indoles with arylsulfinic acids proceeded through a Pd-catalyzed desulfitation reaction. In the presence of an oxidant and an additive, 2-arylindoles were selectively afforded in good yields. Copyright
Differentiation of diastereotopic bromine atoms in SN2 reactions of gem-dibromides
Muenster, Niels,Harms, Klaus,Koert, Ulrich
supporting information; experimental part, p. 1866 - 1867 (2012/02/16)
A novel directed SN2 reaction of conformationally biased gem-dibromides and an arenesulfinate anion is described. The reaction results in the diastereoselective formation of α-bromosulfones. The selectivity originates from pre-coordination of the nucleophile to a free hydroxyl group in the γ-position.
Palladium-catalyzed desulfitative heck-type reaction of aryl sulfinic acids with alkenes
Wang, Guan-Wu,Miao, Tao
supporting information; experimental part, p. 5787 - 5790 (2011/06/23)
An efficient protocol has been developed for the desulfitative Heck-type reaction of aryl sulfinic acids with a variety of alkenes in the presence of a catalytic amount of Pd(OAc)2 and inexpensive Cu(OAc)2 as oxidant. This method does not require a ligand or a base, thereby broadening the scope of Pd-catalyzed coupling reactions. Copyright
Synthesis of ketones by palladium-catalysed desulfitative reaction of arylsulfinic acids with nitriles
Miao, Tao,Wang, Guan-Wu
supporting information; experimental part, p. 9501 - 9503 (2011/10/01)
Palladium-catalysed desulfitative addition of arylsulfinic acids to aryl and alkyl nitriles with 2,2′-bipyridine as a ligand afforded a variety of aryl ketones via hydrolysis of ketimine intermediates.
