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Nickel-Catalyzed Radical Heck-Type C(sp3)-C(sp2) Coupling Cascades Enabled by Bromoalkane-Directed 1,4-Aryl Shift: Access to Olefinated Arylalanines.
Liu, Jian; Hong, Yu; Liu, Yin-Ling; Tan, Jing-Ying; Liu, Hao-Miao; Dai, Gang-Liang; Chen, Shi-Lu; Liu, Ting; Li, Jin-Heng; Tang, Shi.
Afiliación
  • Liu J; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Hong Y; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Liu YL; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Tan JY; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Liu HM; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Dai GL; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Chen SL; Key Laboratory of Cluster Science of Ministry of Education, Beijing Institute of Technology, Beijing 100081, China.
  • Liu T; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
  • Li JH; State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
  • Tang S; College of Chemistry and Chemical Engineering, Jishou University, Jishou 416000, China.
Org Lett ; 24(44): 8192-8196, 2022 Nov 11.
Article en En | MEDLINE | ID: mdl-36318750
ABSTRACT
A bromoalkane-directed radical 1,4-aryl shift strategy for nickel-catalyzed reductive Heck-type C(sp3)-C(sp2) coupling cascades of α-amino-ß-bromocarboxylic acid esters with α-trifluoromethyl alkenes for producing gem-difluorinated arylalanines is presented. The α-aminoalkyl radicals generated from neophyl-type aryl migration function as robust coupling partners to allow for further Giese-type addition with electron-deficient α-trifluoromethyl alkenes and vinyl sulfones, thereby realizing a new radical cascade for the simultaneous installation of an aromatic ring and olefin motif into amino acid backbones.
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Texto completo: 1 Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article
Texto completo
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XML
PubMed Links
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Texto completo: 1 Base de datos: MEDLINE Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2022 Tipo del documento: Article