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• W2180930403 endingPage "149" @default.
• W2180930403 startingPage "139" @default.
• W2180930403 abstract "Saturated heterocycles, such as THFs, pyrrolidines, piperidines and THPs, are essential components of many biologically active compounds. Examples of C–H functionalization on these important ring systems remain scarce, especially at unactivated positions. Here we report the development of conditions for the palladium-catalyzed stereoselective C(sp3)–H arylation at unactivated 3-positions of 5- and 6-membered N- and O-heterocycles with aminoquinoline directing groups. Subtle differences in substrate structures altered their reactivity significantly; and different conditions were required to achieve high yields in each case. Successful conditions were developed using a short empirical optimization approach to cover reaction space with a limited set of variables. Excellent cis-selectivity was achieved in all cases, except for the THP substrate where minor trans-products were formed through a different palladacyclic intermediate. Here, differences in reactivity and selectivity with other directing groups were examined." @default.
• W2180930403 created "2016-06-24" @default.
• W2180930403 creator A5035104027 @default.
• W2180930403 creator A5078788227 @default.
• W2180930403 date "2015-11-27" @default.
• W2180930403 modified "2023-10-15" @default.
• W2180930403 title "Palladium-Catalyzed Directed C(sp³)-H Arylation of Saturated Heterocycles at C-3 Using a Concise Optimization Approach" @default.
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