Ryu, Jaeyune Kwak, Jaesung Shin, Kwangmin Lee, Donggun Chang, Sukbok 2024-01-20T11:34:28Z 2024-01-20T11:34:28Z 2021-08-31 2013-08-28 0002-7863 https://pubs.kist.re.kr/handle/201004/127752 Reported herein is the development of the Ir(III)-catalyzed direct C-H amidation of arenes and alkenes using acyl azides as the nitrogen source. This procedure utilizes an in situ generated cationic half-sandwich iridium complex as a catalyst. The reaction takes place under very mild conditions, and a broad range of sp(2) C-H bonds of chelate group-containing arenes and olefins are smoothly amidated with acyl azides without the intervention of the Curtius rearrangement. Significantly, a wide range of reactants of aryl-, aliphatic-, and olefinic acyl azides were all efficiently amidated with high functional group tolerance. Using the developed approach, Z-enamides were readily accessed with a complete control of regio- and stereoselectivity. The developed direct amidation proceeds in the absence of external oxidants and releases molecular nitrogen as a single byproduct, thus offering an environmentally benign process with wide potential applications in organic synthesis and medicinal chemistry. English AMER CHEMICAL SOC PALLADIUM-CATALYZED AMIDATION SANDWICH IRIDIUM COMPLEXES CCK1 RECEPTOR ANTAGONISTS BOND-FORMING REACTIONS DIRECT AMINATION STEREOSELECTIVE-SYNTHESIS METAL-COMPLEXES ORGANIC AZIDES ARYL AZIDES REGIOSELECTIVE-SYNTHESIS Ir(III)-Catalyzed Mild C-H Amidation of Arenes and Alkenes: An Efficient Usage of Acyl Azides as the Nitrogen Source Article 10.1021/ja406383h 1 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.135, no.34, pp.12861 - 12868 JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 135 34 12861 12868 scie scopus 000323876300059 Chemistry, Multidisciplinary Chemistry Article PALLADIUM-CATALYZED AMIDATION SANDWICH IRIDIUM COMPLEXES CCK1 RECEPTOR ANTAGONISTS BOND-FORMING REACTIONS DIRECT AMINATION STEREOSELECTIVE-SYNTHESIS METAL-COMPLEXES ORGANIC AZIDES ARYL AZIDES REGIOSELECTIVE-SYNTHESIS Organic Chemistry C-H Amidation Acyl Azide Ir(III) Catalyst