Pd(II)-catalyzed chemoselective acetoxylation of C(sp(2))-H and C(sp(3))-H bonds in tertiary amides
| Title | Pd(II)-catalyzed chemoselective acetoxylation of C(sp(2))-H and C(sp(3))-H bonds in tertiary amides |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Vijaykumar, M, Punji, B |
| Journal | Journal of Organic Chemistry |
| Volume | 86 |
| Issue | 12 |
| Pagination | 8172-8181 |
| Date Published | JUN |
| Type of Article | Article |
| ISSN | 0022-3263 |
| Abstract | Palladium-catalyzed chemoselective C(sp(2))-H and C(sp(3))-H acetoxylation of synthetically useful tertiary amides is reported under relatively mild reaction conditions. This protocol proceeds through the assistance of a weakly coordinated directing group (C = O) and requires low catalyst (1.0 mol %) loading. Diverse functionalities, such as C(sp(2))-Cl, C(sp(3))-Cl, -CF3, -COOEt, and -NO2 groups, including morpholinyl, piperazinyl, and pyrrolidinyl heterocycles, are compatible under the reaction conditions. Further functionalization of this protocol is demonstrated by hydrolysis to alcohols, alcohol-acids, as well as reduction to tertiary amines. A preliminary kinetic isotope effect study supported the rate-limiting C-H bond activation process. |
| DOI | 10.1021/acs.joc.1c00629 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 4.354 |
Divison category:
Chemical Engineering & Process Development