Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α‑Amino Esters
Cocatalysis by pivalic acid or copper bromide allows a very fast, clean, and high-yielding palladium-catalyzed coupling of a large array of aryl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO. The study of the reaction conditions, scope, and mechanism is presented. Applied to the...
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| Veröffentlicht in: | Journal of organic chemistry 2012-09, Vol.77 (18), p.7901-7912 |
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| container_end_page | 7912 |
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| container_issue | 18 |
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| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Demory, Emilien Farran, Daniel Baptiste, Benoit Chavant, Pierre Y Blandin, Véronique |
| description | Cocatalysis by pivalic acid or copper bromide allows a very fast, clean, and high-yielding palladium-catalyzed coupling of a large array of aryl, thienyl, and pyridyl halides with cyclic nitrones, including DMPO. The study of the reaction conditions, scope, and mechanism is presented. Applied to the chiral nitrone MiPNO, this transformation provides a straightforward access to enantiopure α-methyl α-arylglycine esters. |
| doi_str_mv | 10.1021/jo301114k |
| format | Article |
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| ispartof | Journal of organic chemistry, 2012-09, Vol.77 (18), p.7901-7912 |
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| language | eng |
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| source | ACS Publications |
| subjects | Chemical Sciences Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Kinetics and mechanisms Organic chemistry Preparations and properties Reactivity and mechanisms |
| title | Fast Pd- and Pd/Cu-Catalyzed Direct C–H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary α‑Amino Esters |
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