Literature DB >> 25650782

I2- or NBS-catalyzed highly efficient α-hydroxylation of ketones with dimethyl sulfoxide.

Yu-Feng Liang1, Kai Wu, Song Song, Xinyao Li, Xiaoqiang Huang, Ning Jiao.   

Abstract

An efficient method for the direct preparation of high synthetic valuable α-hydroxycarbonyls is described. The simple and readily available I2 or NBS was used as catalyst. DMSO acts as the oxidant, oxygen source, and solvent. A diverse range of tertiary Csp(3)-H bonds as well as more challenging secondary Csp(3)-H bonds could be hydroxylated in this transformation. The reaction is mild, less toxic and easy to perform.

Entities:  

Year:  2015        PMID： 25650782     DOI： 10.1021/ol5037387

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  8 in total

1.  Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.

Authors:  Daniel Kaiser; Immo Klose; Rik Oost; James Neuhaus; Nuno Maulide
Journal:  Chem Rev       Date:  2019-06-25       Impact factor: 60.622

2.  α-Functionalisation of Ketones Through Metal-Free Electrophilic Activation.

Authors:  Wojciech Zawodny; Christopher J Teskey; Magdalena Mishevska; Martin Völkl; Boris Maryasin; Leticia González; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2020-09-11       Impact factor: 15.336

3.  PdII-Catalyzed Oxidative Aldehyde-sp2C-H Functionalization and Cyclization Using NHC with Mild Oxidant DMSO for the Selective Synthesis of Esters, Sugar-Based Analogues, and β-Hydroxy Chromanones: An 18O-Labeling Study.

Authors:  Satinath Sarkar; Radha M Laha; Rajendra N Mitra; Dilip K Maiti
Journal:  ACS Omega       Date:  2016-11-21

4.  Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis.

Authors:  Kai Yang; Feng Zhang; Tongchang Fang; Chaokun Li; Wangyang Li; Qiuling Song
Journal:  Nat Commun       Date:  2021-01-19       Impact factor: 14.919

Review 5.  Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis.

Authors:  Ding Lin; Senze Jiang; Ailian Zhang; Tong Wu; Yongchang Qian; Qingsong Shao
Journal:  Nat Prod Bioprospect       Date:  2022-03-07

6.  An iodine/DMSO-catalyzed sequential one-pot approach to 2,4,5-trisubstituted-1H-imidazoles from α-methylene ketones.

Authors:  Janeeka Jayram; Vineet Jeena
Journal:  RSC Adv       Date:  2018-11-07       Impact factor: 3.361

7.  Unexpected Substituent Effects in Spiro-Compound Formation: Steering N-Aryl Propynamides and DMSO toward Site-Specific Sulfination in Quinolin-2-ones or Spiro[4,5]trienones.

Authors:  Xiaoxian Li; Yuanxun Wang; Yaxin Ouyang; Zhenyang Yu; Beibei Zhang; Jingran Zhang; Haofeng Shi; Han Zuilhof; Yunfei Du
Journal:  J Org Chem       Date:  2021-06-29       Impact factor: 4.354

8.  Multistep Photochemical Reactions of Polypyridine-Based Ruthenium Nitrosyl Complexes in Dimethylsulfoxide.

Authors:  Nataliia Marchenko; Pascal G Lacroix; Valerii Bukhanko; Marine Tassé; Carine Duhayon; Martial Boggio-Pasqua; Isabelle Malfant
Journal:  Molecules       Date:  2020-05-08       Impact factor: 4.411
  8 in total

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