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 inOrganic & biomolecular chemistry Vol. 2; no. 1; pp. 113 - 116
Main Authors Li, Guangzhe, Yu, Guo, Wang, Chengdong, Morita, Taiki, Zhang, Xuhai, Nakamura, Hiroyuki
Format Journal Article
Published 22.12.2021
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Summary: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.
Bibliography:10.1039/d1ob02091a
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob02091a