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Enantioselective Construction of C-SCF3 Stereocenters via Nickel Catalyzed Asymmetric Negishi Coupling Reaction.
Hu, Duo-Duo; Nie, Tian-Mei; Xiao, Xi; Li, Kuiliang; Li, Yuan-Bo; Gao, Qian; Bi, Yu-Xiang; Wang, Xi-Sheng.
Affiliation
  • Hu DD; Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
  • Nie TM; School of Chemical and Blasting Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, China.
  • Xiao X; Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
  • Li K; Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
  • Li YB; School of Chemical and Blasting Engineering, Anhui University of Science and Technology, Huainan, Anhui 232001, China.
  • Gao Q; Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
  • Bi YX; Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
  • Wang XS; Hefei National Research Center for Physical Sciences at the Microscale, Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
Angew Chem Int Ed Engl ; 63(15): e202400308, 2024 Apr 08.
Article in En | MEDLINE | ID: mdl-38299744
ABSTRACT
The construction of the SCF3-containing 1,1-diaryl tertiary carbon stereocenters with high enantioselectivities is reported via a nickel-catalyzed asymmetric C-C coupling strategy. This method demonstrates simple operations, mild conditions and excellent functional group tolerance, with newly designed SCF3-containing synthon, which can be easily obtained from commercially available benzyl bromide and trifluoromethylthio anion in a two-step manner. Further substrate exploration indicated that the reaction system could be extended to diverse perfluoroalkyl sulfide (SC2F5, SC3F7, SC4F9, SCF2CO2Et)-substituted 1,1-diaryl compounds with excellent enantioselectivities. The synthetic utility of this transformation was further demonstrated by convenient derivatization to optical SCF3-containing analogues of bioactive compounds without an apparent decrease in enantioselectivity.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl / Angew. Chem. (Int. ed., Internet) / Angewandte Chemie (International ed. Internet) Year: 2024 Document type: Article Affiliation country: China Country of publication: Alemania
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Full text: 1 Collection: 01-internacional Database: MEDLINE Language: En Journal: Angew Chem Int Ed Engl / Angew. Chem. (Int. ed., Internet) / Angewandte Chemie (International ed. Internet) Year: 2024 Document type: Article Affiliation country: China Country of publication: Alemania