4.8 Article

Catalytic Enantioselective Arylation of N-Tosylarylimines with Arylboronic Acids Using C2-Symmetric Cationic N-Heterocyclic Carbene Pd2+ Diaquo Complexes

Journal

ORGANIC LETTERS
Volume 11, Issue 4, Pages 875-878

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol802861s

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Funding

  1. Shanghai Municipal Committee of Science and Technology [06XD14005, 08dj1400100-2]
  2. National Basic Research Program of China [(973)-2009CB825300]
  3. National Natural Science Foundation of China [20472096, 20872162, 20672127, 20732008]

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The asymmetric arylation of N-tosylimines with arylboronic acids was realized by using chiral cationic C-2-symmetric N-heterocyclic carbene (NHC) Pd2+ diaquo complex 5b as the catalyst in combination with 1.0 equiv of K3PO4 center dot 3H(2)O in THF at 4 degrees C in the presence of powdered 4 angstrom MS to afford the corresponding adducts in excellent yields (up to 99%) and good to high enantioselectivities (up to 94% ee).

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