期刊
CHEMICAL COMMUNICATIONS
卷 53, 期 76, 页码 10584-10587出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc06186b
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资金
- Rutgers University
- NSF [CAREER CHE-1650766]
- NSF-MRI [CHE-1229030]
- Direct For Mathematical & Physical Scien [1650766] Funding Source: National Science Foundation
- Division Of Chemistry [1650766] Funding Source: National Science Foundation
Amides are of fundamental interest in many fields of chemistry involving organic synthesis, chemical biology and biochemistry. Here, we report the first catalytic Buchwald-Hartwig coupling of both common esters and amides by highly selective C(acyl)-X (X = O, N) cleavage to rapidly access aryl amide functionality via a cross-coupling strategy. Reactions are promoted by versatile, easily prepared, well-defined Pd-PEPPSI type precatalysts, and proceed in good to excellent yields and with excellent chemoselectivity for the acyl bond cleavage. The method is user friendly because it employs commercially-available, moisture-and air-stable precatalysts. Notably, for the first time we demonstrate selective C(acyl)-N and C(acyl)-O cleavage/Buchwald-Hartwig amination under the same reaction conditions, which allows for streamlining amide synthesis by avoiding restriction to a particular acyl metal precursor. Of broad interest, this study opens the door to using a family of well-defined Pd(II)-NHC precatalysts bearing pyridine throw-away ligands for the selective C(acyl)-amination of bench-stable carboxylic acid derivatives.
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