Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes
An efficient, practical and regioselective synthesis of ( E )-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this metho...
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| Published in | Organic & biomolecular chemistry Vol. 21; no. 25; pp. 5171 - 5175 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Royal Soc Chemistry
28.06.2023
Royal Society of Chemistry |
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| Abstract | An efficient, practical and regioselective synthesis of (
E
)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules.
A copper-catalyzed unprotected hydroxylamine mediated phosphorylation of alkenes furnished structurally important (
E
)-alkenylphosphine oxides under mild reaction conditions with good functional group tolerance and excellent regioselectivity. |
|---|---|
| AbstractList | An efficient, practical and regioselective synthesis of (
E
)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules.
A copper-catalyzed unprotected hydroxylamine mediated phosphorylation of alkenes furnished structurally important (
E
)-alkenylphosphine oxides under mild reaction conditions with good functional group tolerance and excellent regioselectivity. An efficient, practical and regioselective synthesis of ( )-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules. An efficient, practical and regioselective synthesis of (E)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules. An efficient, practical and regioselective synthesis of ( E )-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules. An efficient, practical and regioselective synthesis of (E)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules.An efficient, practical and regioselective synthesis of (E)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons. The reaction will create an opportunity for the synthesis of complex phosphorus containing bioactive molecules. |
| Author | Zhu, Lin Yang, Xin-Xin Wang, Chen-Xi Zhao, Xin-Ming Zhou, Sai-Nan Ren, Wei Zhan, Jun-Long Wang, Bing-Jie Dou, Zao-Zao |
| AuthorAffiliation | Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs. College of Chemistry and Chemical Engineering Anyang Normal University Henan Scientific Research Platform Service Center |
| AuthorAffiliation_xml | – sequence: 0 name: Anyang Normal University – sequence: 0 name: Henan Provincial Engineering and Technology Research Center for Precise Synthesis of Fluorine-Containing Drugs. College of Chemistry and Chemical Engineering – sequence: 0 name: Henan Scientific Research Platform Service Center |
| Author_xml | – sequence: 1 givenname: Jun-Long surname: Zhan fullname: Zhan, Jun-Long – sequence: 2 givenname: Bing-Jie surname: Wang fullname: Wang, Bing-Jie – sequence: 3 givenname: Chen-Xi surname: Wang fullname: Wang, Chen-Xi – sequence: 4 givenname: Xin-Ming surname: Zhao fullname: Zhao, Xin-Ming – sequence: 5 givenname: Sai-Nan surname: Zhou fullname: Zhou, Sai-Nan – sequence: 6 givenname: Zao-Zao surname: Dou fullname: Dou, Zao-Zao – sequence: 7 givenname: Xin-Xin surname: Yang fullname: Yang, Xin-Xin – sequence: 8 givenname: Lin surname: Zhu fullname: Zhu, Lin – sequence: 9 givenname: Wei surname: Ren fullname: Ren, Wei |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/37288792$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1002/adsc.201200853 10.1021/acscatal.9b00832 10.1039/C7OB00505A 10.1021/ol062505l 10.1016/j.bmc.2011.09.058 10.1039/C6RA19002B 10.1055/s-2000-6482 10.1039/C5OB00404G 10.1021/jacs.9b06920 10.1021/om3005614 10.1055/s-1995-5012 10.1021/cr030451c 10.1021/jo052575q 10.1016/S0040-4039(01)01280-1 10.1021/acs.joc.8b01042 10.1021/acs.joc.1c02132 10.1039/C5CC04826E 10.1021/acs.joc.8b00187 10.1021/ol801047k 10.1021/jo5007174 10.1021/bm2004803 10.1016/j.tetlet.2004.04.094 10.1021/ja0494297 10.1021/cr030026j 10.1021/jacs.8b00550 10.1021/ol027515a 10.1039/C3RA45212C 10.1055/s-1988-27466 10.1039/C0CC01617A 10.1021/jo501321m 10.1021/jo00240a049 10.1002/adsc.201400123 10.1016/j.jorganchem.2009.06.020 10.1002/chem.201003561 10.1021/jacs.6b01337 10.1021/jo010337z 10.1002/ejoc.201900144 10.1021/cr100244e 10.1016/j.cellsig.2010.05.022 10.1021/ma9707289 10.1016/S0040-4039(00)82487-9 10.1021/ol0474047 10.1002/asia.200800035 10.1039/D2OB01922A 10.1002/1521-3773(20010518)40:10<1929::AID-ANIE1929>3.0.CO;2-M 10.1021/ar400071v 10.1039/B613416E 10.1021/ja101585z 10.1021/jo025725v 10.1021/ol502009b 10.1016/j.polymer.2008.07.059 10.1002/ajoc.201700434 10.1002/adsc.202300108 10.1021/ol047516y 10.1055/s-0034-1379545 10.1021/jm7014793 10.1021/cr040179m 10.1021/acs.joc.6b02181 10.1039/b613416e 10.1039/c5cc04826e 10.1039/c6ra19002b 10.1039/d2ob01922a 10.1039/c7ob00505a 10.1039/c0cc01617a 10.1039/c3ra45212c 10.1039/c5ob00404g |
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| Keywords | HYDROPHOSPHORYLATION PHOSPHONATES ACIDS H-PHOSPHINE OXIDES VINYLPHOSPHINE OXIDES BONDS 1,1-DIBROMO-1-ALKENES TERMINAL ALKYNES SELECTIVE SYNTHESIS DIPHENYLPHOSPHINE OXIDE |
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publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo5007174 – volume: 365 start-page: 1678 year: 2023 ident: WOS:000986629600001 article-title: TEMPO Mediated Cyclopropanols Ring Opening C-N Cross-Coupling with Nitrogen Nucleophiles publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.202300108 |
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| Snippet | An efficient, practical and regioselective synthesis of (
E
)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and... An efficient, practical and regioselective synthesis of (E)-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and... An efficient, practical and regioselective synthesis of ( )-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and... |
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| SubjectTerms | Alkenes Catalysis Chemical synthesis Chemistry Chemistry, Organic Copper Functional groups Oxidation Phosphorylation Physical Sciences Regioselectivity Science & Technology |
| Title | Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes |
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