Photoinduced C(sp3)-H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer
| dc.contributor.author | Niu, Ben | |
| dc.contributor.author | Sachidanandan, Krishnakumar | |
| dc.contributor.author | Cooke, Maria Victoria | |
| dc.contributor.author | Casey, Taylor E. | |
| dc.contributor.author | Laulhé, Sébastien | |
| dc.contributor.department | Chemistry and Chemical Biology, School of Science | |
| dc.date.accessioned | 2023-09-25T11:26:00Z | |
| dc.date.available | 2023-09-25T11:26:00Z | |
| dc.date.issued | 2022 | |
| dc.description.abstract | A photoinduced, iron(III) chloride-catalyzed C-H activation of N-methyl amides and ethers leads to the formation of C-S and C-Se bonds via a ligand-to-metal charge transfer (LMCT) process. This methodology converts secondary and tertiary amides, sulfonamides, and carbamates into the corresponding amido-N,S-acetal derivatives in good yields. Mechanistic work revealed that this transformation proceeds through a hydrogen atom transfer (HAT) involving chlorine radical intermediates. | |
| dc.eprint.version | Author's manuscript | |
| dc.identifier.citation | Niu B, Sachidanandan K, Cooke MV, Casey TE, Laulhé S. Photoinduced C(sp3)-H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer. Org Lett. 2022;24(25):4524-4529. doi:10.1021/acs.orglett.2c01505 | |
| dc.identifier.uri | https://hdl.handle.net/1805/35738 | |
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society | |
| dc.relation.isversionof | 10.1021/acs.orglett.2c01505 | |
| dc.relation.journal | Organic Letters | |
| dc.rights | Publisher Policy | |
| dc.source | PMC | |
| dc.subject | Amides | |
| dc.subject | Ethers | |
| dc.subject | Ferric compounds | |
| dc.subject | Hydrogen | |
| dc.subject | Ligands | |
| dc.title | Photoinduced C(sp3)-H Chalcogenation of Amide Derivatives and Ethers via Ligand-to-Metal Charge-Transfer | |
| dc.type | Article |