77144-79-7Relevant academic research and scientific papers
Electrochemical-Induced Hydroxysulfonylation of α-CF3 Alkenes to Access Tertiary β-Hydroxysulfones
Luo, Xu,Wang, Shengchun,Lei, Aiwen
, p. 1016 - 1022 (2022/02/07)
An electrochemical hydroxysulfonylation of α-CF3 alkenes was accomplished in this work. By using easily available sodium sulfinates as the sulfonylating agents, a series of valuable α-trifluoromethyl tertiary alcohols were synthesized under mild and environmentally friendly electrolysis conditions in moderate to good yields. The preliminary mechanistic investigation indicates that this difunctional reaction involves a radical process via a sulfonyl radical. Gram-scale synthesis shows the significant potential application of this protocol. (Figure presented.).
Visible-light-induced sequential sulfonylation/hydroxylation of allylacetamides leading to β-tert-hydroxy sulfones
Qian, Zhu-Ming,Zuo, Kai-Li,Guan, Zhi,He, Yan-Hong
supporting information, (2021/02/27)
A mild method for the sequential sulfonylation/hydroxylation process of allylacetamides has been developed, in which sulfonyl radicals can be generated from easily available arylsulfinic acids by using eosin Y as an organic photocatalyst under visible-lig
Electrochemical synthesis of β-hydroxy-, β-alkoxy-, and β-carbonyloxy sulfones by vicinal difunctionalization of olefins
Zhang, Zhefan,Yan,Ma, Dengke,Sun, Jianwei
supporting information, p. 1509 - 1511 (2019/05/04)
An electrochemical vicinal heterodifunctionalization of olefins for the synthesis of β-oxysulfones is described. With suitable choice of the conditions, including current, electrodes, and electrolyte, this oxidation reaction proceeded efficiently in an un
Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation
Yan, Qiaozhi,Xiao, Guiying,Wang, Ying,Zi, Guofu,Zhang, Zhanbin,Hou, Guohua
supporting information, p. 1749 - 1756 (2019/01/25)
A highly efficient and enantioselective Rh-(R,R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-(R,R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[b]thiophene-1,1-dioxides were successfully hydrogenated to the corresponding chiral sulfones with excellent enantioselectivities (up to 99.4% ee) regardless of the steric hindrance, electronic property, and geometry of the substrates. Moreover, this reaction offers a route to (S)-(+)-ar-turmerone as a spice flavor, which is an important synthetic intermediate of pharmaceuticals.
PQS-enabled visible-light iridium photoredox catalysis in water at room temperature
Bu, Mei-Jie,Cai, Chun,Gallou, Fabrice,Lipshutz, Bruce H.
supporting information, p. 1233 - 1237 (2018/03/26)
An amphoteric PQS-attached photocatalyst has been prepared that undergoes self-aggregation in water into nanomicelles. This covalently bound species enables Ir-based photoredox catalysis to be conducted in the absence of additives or co-solvents. Representative reactions are described using this new catalytic system, which require no additional investment of external energy in the form of heating or cooling. The entire aqueous reaction mixture readily undergoes in-flask recycling and thus, represents a sustainable precious metal technology.
An Efficient Organic Electrosynthesis of β-Hydroxysulfones
Chan, Chieh-Kai,Lo, Nai-Chang,Chen, Po-Yu,Chang, Meng-Yang
, p. 4469 - 4477 (2017/09/26)
An efficient organic electrosynthesis of tertiary β-hydroxysulfones from functionalized α-methylstyrenes with substituted sodium sulfinates has been established. The novel electrosynthetic method provided the desired products in excellent yields, and the key structure was confirmed by X-ray single-crystal diffraction analysis.
Synthesis of β-Hydroxysulfones from Sulfonyl Chlorides and Alkenes Utilizing Visible Light Photocatalytic Sequences
Pagire, Santosh K.,Paria, Suva,Reiser, Oliver
supporting information, p. 2106 - 2109 (2016/06/01)
The synthesis of β-hydroxysulfones from sulfonyl chlorides and styrenes in the presence of water by a visible light mediated atom transfer radical addition (ATRA)-like process utilizing fac[Ir(ppy)3] as photoredox catalyst was developed in high
Aerobic oxysulfonylation of alkenes leading to secondary and tertiary β-hydroxysulfones
Lu, Qingquan,Zhang, Jian,Wei, Fuliang,Qi, Yue,Wang, Huamin,Liu, Zhiliang,Lei, Aiwen
supporting information, p. 7156 - 7159 (2013/07/26)
New channel! A novel and attractive dioxygen activation by sulfinic acids was explored that is capable of performing efficiently without the assistance of transition metals or radical initiators. This reaction furnishes secondary and tertiary β-hydroxysulfones under mild conditions; β-hydroperoxysulfone was isolated as an important intermediate. Copyright
Iron-catalyzed sulfonyl radical formations from sulfonylhydrazides and oxidative addition to alkenes
Taniguchi, Tsuyoshi,Idota, Atsushi,Ishibashi, Hiroyuki
experimental part, p. 3151 - 3153 (2011/05/12)
Generation of sulfonyl radicals from sulfonylhydrazides has been achieved in the presence of a non-toxic iron catalyst and oxygen. The intermolecular addition of resultant sulfonyl radicals to alkenes affords β-hydroxysulfone compounds.
