N-aroylsulfonamide-photofragmentation (ASAP)
- The photochemical fragmentation of N-aroylsulfonamides 9 (ASAP) is a powerful method for the preparation of various biaryls. Compounds 9 are easily accessible in two steps from amines by treatment with arenesulfonyl chlorides and aroyl chlorides. Many of these compounds were prepared for the first time. The irradiation takes place in a previously developed continuous-flow reactor using inexpensive UVB or UVC fluorescent lamps. Isocyanates and sulphur dioxide are formed as the only by-products. The ASAP tolerates a variety of functional groups and is even suited for the preparation of phenylnaphthalenes and terphenyls. The ASAP mechanism was elucidated by interaction of photophysical and quantum chemical (DFT) methods and revealed a spirocyclic biradical as key intermediate.
| Author details: | Pablo WessigORCiDGND, Saskia Krebs |
|---|---|
| DOI: | https://doi.org/10.1002/ejoc.202100955 |
| ISSN: | 1434-193X |
| ISSN: | 1099-0690 |
| Title of parent work (English): | European journal of organic chemistry |
| Subtitle (English): | a versatile route to biaryls |
| Publisher: | Wiley-VCH |
| Place of publishing: | Weinheim |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2021/09/22 |
| Publication year: | 2021 |
| Release date: | 2022/10/13 |
| Tag: | Biaryls; Fragmentation; Isocyanates; Photochemistry; Sulfonamides |
| Volume: | 2021 |
| Issue: | 46 |
| Number of pages: | 8 |
| First page: | 6367 |
| Last Page: | 6374 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
