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Abstract Enantioselective, intermolecular alkene arylamination was achieved through gold redox catalysis. Screening of ligands revealed chiral P,N ligands as the optimal choice, giving alkene aminoarylation with good yields (up to 80 %) and excellent stereoselectivity (up to 99 : 1er). As the first example of enantioselective gold redox catalysis, this work confirmed the feasibility of applying a chiral ligand at the gold(I) stage, with the stereodetermining step (SDS) at the gold(III) intermediate, thus opening up a new way to conduct gold redox catalysis with stereochemistry control.
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Gold redox catalysis for cyclization/arylation of allylic oximes: synthesis of isoxazoline derivatives
Base-assisted diazonium activation has been employed to promote gold( i )/( iii ) redox catalysis toward allylic oxime cyclization/aryl coupling. Functional isoxazolines were prepared with good to excellent yields, while the alternative photoactivation method provided trace amounts of the isoxazoline products. This study further broadens the scope of gold redox chemistry.
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- Award ID(s):
- 1665122
- PAR ID:
- 10103982
- Date Published:
- Journal Name:
- Chemical Communications
- Volume:
- 55
- Issue:
- 56
- ISSN:
- 1359-7345
- Page Range / eLocation ID:
- 8150 to 8153
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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- Free Publicly Accessible Full Text
-
Accepted Manuscript1.0
- Journal Article:
- https://doi.org/10.1039/c9cc02830g
