Copper()-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling of -propargylanilines with phosphites
Intramolecular hydroarylation-redox cross-dehydrogenative coupling of N -propargylanilines with phosphite diesters proceeded in the presence of Cu( i )-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds...
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| Published in | Organic & biomolecular chemistry Vol. 2; no. 1; pp. 113 - 116 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Published |
22.12.2021
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| Online Access | Get full text |
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| Abstract | Intramolecular hydroarylation-redox cross-dehydrogenative coupling of
N
-propargylanilines with phosphite diesters proceeded in the presence of Cu(
i
)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
A simple method for site-selective synthesis of 2-phosphonotetrahydroquinolines. Tetrahydroquinoline was constructed by a cyclization reaction and in the meantime the phosphoric acid (ester) group was introduced to the C2-position. |
|---|---|
| AbstractList | Intramolecular hydroarylation-redox cross-dehydrogenative coupling of
N
-propargylanilines with phosphite diesters proceeded in the presence of Cu(
i
)-catalysts (20 mol%) to selectively give 2-phosphono-1,2,3,4-tetrahydroquinolines in good yields with 100% atomic utilization. P-H and two C-H bonds are activated at once and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.
A simple method for site-selective synthesis of 2-phosphonotetrahydroquinolines. Tetrahydroquinoline was constructed by a cyclization reaction and in the meantime the phosphoric acid (ester) group was introduced to the C2-position. |
| Author | Wang, Chengdong Nakamura, Hiroyuki Li, Guangzhe Morita, Taiki Yu, Guo Zhang, Xuhai |
| AuthorAffiliation | School of Chemical Engineering Department of Nuclear Medicine Department of Pharmaceutical Sciences Tokyo Institute of Technology Institute of Innovative Research Laboratory for Chemistry and Life Science State Key Laboratory of Fine Chemicals Dalian University of Technology First Affiliated Hospital of Dalian Medical University |
| AuthorAffiliation_xml | – name: State Key Laboratory of Fine Chemicals – name: Department of Nuclear Medicine – name: Laboratory for Chemistry and Life Science – name: Tokyo Institute of Technology – name: Department of Pharmaceutical Sciences – name: School of Chemical Engineering – name: Dalian University of Technology – name: First Affiliated Hospital of Dalian Medical University – name: Institute of Innovative Research |
| Author_xml | – sequence: 1 givenname: Guangzhe surname: Li fullname: Li, Guangzhe – sequence: 2 givenname: Guo surname: Yu fullname: Yu, Guo – sequence: 3 givenname: Chengdong surname: Wang fullname: Wang, Chengdong – sequence: 4 givenname: Taiki surname: Morita fullname: Morita, Taiki – sequence: 5 givenname: Xuhai surname: Zhang fullname: Zhang, Xuhai – sequence: 6 givenname: Hiroyuki surname: Nakamura fullname: Nakamura, Hiroyuki |
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| ContentType | Journal Article |
| DOI | 10.1039/d1ob02091a |
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| Snippet | Intramolecular hydroarylation-redox cross-dehydrogenative coupling of
N
-propargylanilines with phosphite diesters proceeded in the presence of Cu(
i... |
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| Title | Copper()-catalysed intramolecular hydroarylation-redox cross-dehydrogenative coupling of -propargylanilines with phosphites |
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