PPh3/Selectfluor‐Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis
By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The develop...
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| Published in | European journal of organic chemistry Vol. 2019; no. 34; pp. 5998 - 6002 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
15.09.2019
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| Abstract | By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols.
An efficient synthesis of acid anhydrides or acyl fluorides mediated by PPh3/Selectfluor synstem is reported. Mechanistic studies show that the reaction proceeds through active species of acyloxyphosphonium ions, which can be quickly converted into the final products in situ by a second carboxylic acid or F–. |
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| AbstractList | By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols. By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can selectively react with a second carboxylic acid or fluoride to in situ yield the corresponding acid anhydrides or acyl fluorides. The developed protocol features commercially availabile reagents, no involvement of base, room temperature conditions, and simple experimental procedure. Additionally, various amides or esters are readily achieved, respectively, with the addition of amines or alcohols. An efficient synthesis of acid anhydrides or acyl fluorides mediated by PPh3/Selectfluor synstem is reported. Mechanistic studies show that the reaction proceeds through active species of acyloxyphosphonium ions, which can be quickly converted into the final products in situ by a second carboxylic acid or F–. |
| Author | Yang, Zhen Chen, Siwei Yan, Yizhe Tang, Lin Zhou, Qiuju Dou, You Yang, Fang Zhang, Chenxi |
| Author_xml | – sequence: 1 givenname: Zhen surname: Yang fullname: Yang, Zhen organization: Xinyang Normal University – sequence: 2 givenname: Siwei surname: Chen fullname: Chen, Siwei organization: Xinyang Normal University – sequence: 3 givenname: Fang surname: Yang fullname: Yang, Fang organization: Xinyang Normal University – sequence: 4 givenname: Chenxi surname: Zhang fullname: Zhang, Chenxi organization: Xinyang Normal University – sequence: 5 givenname: You surname: Dou fullname: Dou, You organization: Xinyang Normal University – sequence: 6 givenname: Qiuju surname: Zhou fullname: Zhou, Qiuju organization: Xinyang Normal University – sequence: 7 givenname: Yizhe surname: Yan fullname: Yan, Yizhe organization: Zhengzhou University of Light Industry – sequence: 8 givenname: Lin orcidid: 0000-0003-0477-2481 surname: Tang fullname: Tang, Lin email: lintang@xynu.edu.cn organization: Xinyang Normal University |
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| Keywords | REAGENT MITSUNOBU ACYLATION TRIFLUORIDE Acyl fluorides Carboxylic acids FLUORINATION Triphenylphosphine Acid anhydrides MILD ALCOHOLS Selectfluor DEHYDRATION CHLORIDES EFFICIENT |
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| Snippet | By taking the advantage of PPh3/Selectfluor system, carboxylic acids are efficiently converted into the pivotal intermediates acyloxyphosphonium ions that can... |
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| SubjectTerms | Acid anhydrides Acidic oxides Acyl fluorides Alcohols Amides Amines Carboxylic acids Chemistry Chemistry, Organic Esters Fluorides Physical Sciences Reagents Science & Technology Selectfluor Triphenylphosphine |
| Title | PPh3/Selectfluor‐Mediated Transformation of Carboxylic Acids into Acid Anhydrides and Acyl Fluorides and Its Application in Amide and Ester Synthesis |
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