Pd-PEPPSI: A General Pd-NHC Precatalyst for Suzuki–Miyaura Cross-Coupling of Esters by C–O Cleavage
- Award ID(s):
- 1650766
- NSF-PAR ID:
- 10055408
- Date Published:
- Journal Name:
- Organometallics
- Volume:
- 36
- Issue:
- 19
- ISSN:
- 0276-7333
- Page Range / eLocation ID:
- 3784 to 3789
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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N-Acyl-hydantoins have emerged as novel acyl transfer reagents for the synthesis of ketones via selective N–C(O) cleavage. Herein, we report two new protocols for the cross-coupling of N-acyl-5,5-dimethylhydantoins using versatile and readily accessible Pd–PEPPSI or Pd/phosphine catalysts. The acyl Suzuki reactions afford biaryl ketones in good to excellent yields under operationally-simple conditions using commercially-available, bench- and air-stable twisted N-acyl-hydantoins as acyl donors. The method complements and expands on the previous protocol for the cross-coupling of N-acyl-hydantoins (Org. Process Res. Dev. 2018, 22, 1188).more » « less