Site-Selective C–H Functionalization of N‑Aryl and N‑Heteroaryl Piperidines, Morpholines, and Piperazines Controlled by a Chiral Dirhodium Tetracarboxylate Catalyst

Rhodium-catalyzed C–H insertion by donor/acceptor carbenes is a useful transformation in organic synthesis. However, the site-selectivity of the C–H transformation on the target molecule is often a major issue. Site-selective C–H functionalizations of challenging substrates like N-aryl- and N-hetero...

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Bibliographic Details
Published inACS catalysis Vol. 13; no. 4; pp. 2359 - 2366
Main Authors Korvorapun, Korkit, Boni, Yannick T., Maier, Thomas C., Bauer, Armin, Licher, Thomas, Macor, John E., Derdau, Volker, Davies, Huw M. L.
Format Journal Article
LanguageEnglish
Published American Chemical Society 17.02.2023
Subjects
C−H functionalization
regioselectivity
morpholines
stereoselectivity
piperidines
piperazines
rhodium
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Summary:Rhodium-catalyzed C–H insertion by donor/acceptor carbenes is a useful transformation in organic synthesis. However, the site-selectivity of the C–H transformation on the target molecule is often a major issue. Site-selective C–H functionalizations of challenging substrates like N-aryl- and N-heteroaryl piperidines could be achieved through chiral rhodium carbene intermediates, leading to the formation of highly stereoselective C-2 products. In addition, N-aryl morpholines and piperazines were selectively reacted at the α position to the N-aryl group.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.2c05283