Stereoselective Palladium‐Catalyzed C( <i>sp</i> <sup>3</sup> )−H Mono‐Arylation of Piperidines and Tetrahydropyrans with a C(4) Directing Group
نویسندگان
چکیده
A selective Pd-catalyzed C(3)−H cis-functionalization of piperidine and tetrahydropyran carboxylic acids is achieved using a C(4) aminoquinoline amide auxiliary. High mono- cis-selectivity attained by mesityl acid as an additive. Conditions are developed with significantly lower reaction temperatures (≤50 °C) than other reported heterocycle C(sp3)−H functionalization reactions, which facilitated DoE optimization. one-pot C−H functionalization-epimerization procedure provides the trans-3,4-disubstituted isomers directly. Divergent removal accomplished installation acid, alcohol, nitrile functional groups. Overall, fragment compounds suitable for screening generated in 3–4 steps from readily-available heterocyclic acids.
منابع مشابه
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ژورنال
عنوان ژورنال: Advanced Synthesis & Catalysis
سال: 2022
ISSN: ['1615-4169', '1615-4150']
DOI: https://doi.org/10.1002/adsc.202200030