The palladium-catalyzed Suzuki-Miyaura cross-coupling of Nacylsuccinimides as versatile acyl-transfer reagents via selective amide N–C bond cleavage is reported. The method is user-friendly since it employs commercially-available, air-stable reagents and catalysts. The cross-coupling is enabled by half-twist of the amide bond in N-acylsuccinimides. These highly effective, crystalline acyltransfer reagents present major advantages over perpendicularly twisted N-acylglutarimides, including low price of the succinimide activating ring, selective metal insertion under redox neutral conditions and high stability of the amide bond towards reaction conditions. Mechanistic studies indicate that oxidative addition is the rate limiting step in this widely applicable protocol.
more »
« less
N -Acyl-Glutarimides: Privileged Scaffolds in Amide N-C Bond Cross-Coupling: N -Acyl-Glutarimides: Privileged Scaffolds in Amide N-C Bond Cross-Coupling
- Award ID(s):
- 1650766
- PAR ID:
- 10055163
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- European Journal of Organic Chemistry
- Volume:
- 2018
- Issue:
- 20-21
- ISSN:
- 1434-193X
- Page Range / eLocation ID:
- 2352 to 2365
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
-
Abstract This Graphical Review provides an overview of amide bond activation achieved by selective oxidative addition of the N–C(O) acyl bond to transition metals and nucleophilic acyl addition, resulting in acyl and decarbonylative coupling, together with key mechanistic details pertaining to amide bond distortion underlying this reactivity manifold.more » « less
An official website of the United States government
