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Enantioselective Synthesis of N-Benzylic Heterocycles by Ni/Photoredox Dual Catalysis.
Lacker, Caitlin R; DeLano, Travis J; Chen, Emily P; Kong, Jongrock; Belyk, Kevin M; Piou, Tiffany; Reisman, Sarah E.
Affiliation
  • Lacker CR; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • DeLano TJ; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Chen EP; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
  • Kong J; Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
  • Belyk KM; Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
  • Piou T; Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
  • Reisman SE; The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
J Am Chem Soc ; 144(44): 20190-20195, 2022 11 09.
Article in En | MEDLINE | ID: mdl-36288571
ABSTRACT
An asymmetric cross-coupling of α-N-heterocyclic trifluoroborates with aryl bromides using Ni/photoredox dual catalysis has been developed. This C(sp2)-C(sp3) cross-coupling provides access to pharmaceutically relevant chiral N-benzylic heterocycles in good to excellent enantioselectivity when bioxazolines (BiOX) are used as the chiral ligand. High-throughput experimentation significantly streamlined reaction development by identifying BiOX ligands for further investigation and by allowing for rapid optimization of conditions for new trifluoroborate salts.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Bromides / Nickel Language: En Journal: J Am Chem Soc Year: 2022 Document type: Article Affiliation country:
Fulltext
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Bromides / Nickel Language: En Journal: J Am Chem Soc Year: 2022 Document type: Article Affiliation country: