4.8 Article

Transformation of Thioacids into Carboxylic Acids via a Visible-Light-Promoted Atomic Substitution Process

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ORGANIC LETTERS
卷 24, 期 10, 页码 2020-2024

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c00481

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资金

  1. School-level Projects [2020010, 2020021]
  2. Doctoral Start-up Foundation of Jilin Institute of Chemical Technology [2021016]
  3. Liaoning Revitalization Talents Program [XLYC1902111]
  4. Key projects of Department of Education, Liaoning Province [LZD202005]
  5. Project of Science and Technology Develop-ment of Jilin Province [20190303116SF, 202002008JC]
  6. Project of the Education Department of Jilin Province [JJKH20210242KJ]

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A visible-light-promoted atomic substitution reaction has been developed for transforming thiocacids into carboxylic acids using DMSO as the oxygen source, resulting in over 90% yields of various alkyl and aryl carboxylic acids. The reaction proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO.
A visible-light-promoted atomic substitution reaction for transforming thiocacids into carboxylic acids with dimethyl sulfoxide (DMSO) as the oxygen source has been developed, affording various alkyl and aryl carboxylic acids in over 90% yields. The atomic substitution process proceeds smoothly through the photochemical reactivity of the formed hydrogen-bonding adduct between thioacids and DMSO. A DMSO-involved proton-coupled electron transfer (PCET) and the simultaneous generation of thiyl and hydroxyl radicals are proposed to be key steps for realizing the transformation.

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