Iridium-catalyzed reductive β-alkylation of (iso)quinoline derivatives by an enone-trapping strategy
By employing [IrCp*Cl 2 ] 2 /Mg(OMe) 2 /(CH 2 O) n as an applicable catalyst system, we report a reductive β-alkylation of (iso)quinolinium salts with cost-effective and readily available β-chloro ketones, proceeding with good chemoselectivity, mild reaction conditions, and without the need for intr...
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| Published in | Organic & biomolecular chemistry Vol. 22; no. 22; pp. 4516 - 452 |
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| Main Authors | , , |
| Format | Journal Article |
| Published |
05.06.2024
|
| Online Access | Get full text |
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| Summary: | By employing [IrCp*Cl
2
]
2
/Mg(OMe)
2
/(CH
2
O)
n
as an applicable catalyst system, we report a reductive β-alkylation of (iso)quinolinium salts with cost-effective and readily available β-chloro ketones, proceeding with good chemoselectivity, mild reaction conditions, and without the need for introduction of a substituent at position-3 of the quinolyl skeleton. Mechanistic investigations suggest that the reaction proceeds
via
a sequence of hydride transfer-initiated dearomatization of (iso)quinolinium salts,
in situ
enamine-trapping of enone and a second round of hydride transfer to the coupling adducts. The present work offers an important complement to the synthesis of functionalized (iso)tetrahydroquinolines.
Here, we report an iridium-catalyzed reductive β-alkylation of (iso)quinolinium salts with β-chloro ketones, which offers an important complement to the synthesis of functionalized (iso)tetrahydroquinolines. |
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| Bibliography: | Electronic supplementary information (ESI) available: Experimental details and NMR spectra of all compounds. See DOI https://doi.org/10.1039/d4ob00666f |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/d4ob00666f |