Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 17, Pages 3022-3028Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201700542
Keywords
remote CH activation; rhodium; alkylation; quinoline N-oxide; olefin; EP4 agonist
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Funding
- SERB-DST [EMR/2014/001023]
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Reported herein is a rhodium(III)-catalyzed regioselective distal C(sp2)-H bond alkylation of quinoline N-oxides using olefins as alkyl source and N-oxide as the traceless directing group. The reaction exhibits broad substrate scope with excellent selectivity for C-8 position and good yields of alkylated products. The usefulness of the developed catalytic protocol is established by synthesis of EP4 agonist. In mechanistic study, C-8 olefinated quinoline was identified as the reaction intermediate, which gets reduced to desired C-8 alkylated product in the presence of a rhodium(I) species (produced from rhodium(III) during reaction) and formic acid. Formic acid is produced from dimethylformamide in the presence of silver tetrafluoroborate.
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