4.8 Article

Palladium-Catalyzed Benzylic Phosphorylation of Diarylmethyl Carbonates

Journal

ORGANIC LETTERS
Volume 20, Issue 12, Pages 3553-3556

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01323

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Funding

  1. JSPS KAKENHI [JP 15H05485, JP 17H06092]

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A palladium-catalyzed benzylic substitution of tert-butyl diarylmethyl carbonates with a pinacol-derived H-phosphonate proceeds to deliver the corresponding benzylic phosphorylated products in good yields. Moreover, the asymmetric synthesis is possible via a Pd/(R-p,R-p')-(S)-Mandyphos-catalyzed kinetic resolution-DYKAT (dynamic kinetic asymmetric transformation) sequence, and optically active alpha-chiral diarylmethylphosphonates are obtained with synthetically useful yields and enantiomeric ratios (up to 50% and 92:8 er).

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