| Autor: |
Injamam Ul Hoque, Apurba Samanta, Shyamal Pramanik, Soumyadeep Roy Chowdhury, Rabindranath Lo, Soumitra Maity |
| Jazyk: |
angličtina |
| Rok vydání: |
2024 |
| Předmět: |
|
| Zdroj: |
Nature Communications, Vol 15, Iss 1, Pp 1-12 (2024) |
| Druh dokumentu: |
article |
| ISSN: |
2041-1723 |
| DOI: |
10.1038/s41467-024-49279-w |
| Popis: |
Abstract Controlling the ambident reactivity of thiocyanates in reaction manifolds has been a long-standing and formidable challenge. We report herein a photoredox strategy for installing thiocyanates and isothiocyanates in a controlled chemoselective fashion by manipulating the ambident-SCN through catalyst modulation. The methodology allows redox-, and pot-economical ‘on-demand’ direct access to both hydrothiophene and pyrrolidine heterocycles from the same feedstock alkenes and bifunctional thiocyanomalonates in a photocascade sequence. Its excellent chemoselectivity profile was further expanded to access Se- and N-heterocycles by harnessing selenonitriles. Redox capability of the catalysts, which dictates the substrates to participate in a single or cascade catalytic cycle, was proposed as the key to the present chemodivergency of this process. In addition, detailed mechanistic insights are provided by a conjugation of extensive control experiments and dispersion-corrected density functional theory (DFT) calculations. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
|
Full text from SpringerLink