Visible-light-mediated amidation from carboxylic acids and tertiary amines <i>via</i> C–N cleavage
Chengyihan Gu, Shuaishuai Wang, Qingran Zhang, Jin Xie
Abstract
In this communication, we report a photocatalyzed amidation strategy from carboxylic acids and tertiary amines through C-N bond cleavage. A wide scope of structurally diverse carboxylic acids participate smoothly in the reaction, providing the desired tertiary amides with moderate-to-good yields (34 examples, up to 93% yield). This amidation strategy provides an alternative way to address the regioselectivity between nucleophilic functional groups, thus complementing the functional group compatibility of classical amidation protocols. Its synthetic robustness is also proved by the late-stage modification of several complex molecules and gram-scale applications.
Topics & Concepts
ChemistryRegioselectivityNucleophileFunctional groupCombinatorial chemistryBond cleavageCarboxylic acidCleavage (geology)MoleculeOrganic chemistryCatalysisPolymerEngineeringGeotechnical engineeringFracture (geology)Radical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling Reactions