Literature DB >> 27564642

Conversion of Simple Cyclohexanones into Catechols.

Yu-Feng Liang1, Xinyao Li1, Xiaoyang Wang1, Miancheng Zou1, Conghui Tang1, Yujie Liang1, Song Song1, Ning Jiao1,2.   

Abstract

A novel I2-catalyzed direct conversion of cyclohexanones to substituted catechols under mild and simple conditions has been described. This novel transformation is remarkable with the multiple oxygenation and dehydrogenative aromatization processes enabled just by using DMSO as the solvent, oxidant, and oxygen source. This metal-free and simple system demonstrates a versatile protocol for the synthesis of highly valuable substituted catechols and therefore streamlines the synthesis and modification of biologically important molecules for drug discovery.

Entities:  

Year:  2016        PMID: 27564642     DOI: 10.1021/jacs.6b07269

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  6 in total

1.  Synthesis and Evaluation of Marine Natural Product-Inspired Meroterpenoids with Selective Activity toward Dormant Mycobacterium tuberculosis.

Authors:  Anshupriya Si; Alexander D Landgraf; Sandra Geden; Steven J Sucheck; Kyle H Rohde
Journal:  ACS Omega       Date:  2022-06-27

2.  Total Synthesis and Computational Investigations of Sesquiterpene-Tropolones Ameliorate Stereochemical Inconsistencies and Resolve an Ambiguous Biosynthetic Relationship.

Authors:  Christopher Y Bemis; Chad N Ungarean; Alexander S Shved; Cooper S Jamieson; Taehwan Hwang; Ken S Lee; K N Houk; David Sarlah
Journal:  J Am Chem Soc       Date:  2021-04-07       Impact factor: 16.383

3.  Differentiation between enamines and tautomerizable imines in the oxidation reaction with TEMPO.

Authors:  Xiaoming Jie; Yaping Shang; Zhe-Ning Chen; Xiaofeng Zhang; Wei Zhuang; Weiping Su
Journal:  Nat Commun       Date:  2018-11-27       Impact factor: 14.919

Review 4.  Synthesis of polysubstituted arenes through organocatalytic benzannulation.

Authors:  Qian Zhao; Cheng Peng; Gu Zhan; Bo Han
Journal:  RSC Adv       Date:  2020-11-10       Impact factor: 4.036

5.  (NHC)Pd(II) hydride-catalyzed dehydroaromatization by olefin chain-walking isomerization and transfer-dehydrogenation.

Authors:  Weihao Chen; Yang Chen; Xiao Gu; Zaizhu Chen; Chun-Yu Ho
Journal:  Nat Commun       Date:  2022-09-20       Impact factor: 17.694

6.  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

  6 in total

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