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Blue light-promoted photolysis of aryldiazoacetates† †Electronic supplementary information (ESI) available. CCDC 1824108. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8sc01165f
| Content Provider | Semantic Scholar |
|---|---|
| Author | Jurberg, Igor D. Davies, Huw M. L. |
| Copyright Year | 2018 |
| Abstract | The chemistry of diazocompounds has been intensively studied over the past decades. Today, a number of catalytic, racemic thermal processes, as well as highly stereoselective methods describing cyclopropanations, O–H, N–H and C–H insertions, (formal) cycloadditions and rearrangements have been established, thus allowing the straightforward preparation of a variety of molecules. In contrast to the numerous protocols reported on thermal processes, photochemical studies with diazocompounds have been performed mostly several decades ago, and modern applications are relatively scarce. Among these, Suero and co-workers have recently demonstrated that a hypervalent iodine reagent carrying a diazoacetate moiety could be employed in a photoredox-catalyzed protocol for the C–H functionalization of a variety of arenes. In the sequence, the diazocompounds produced could be further engaged in classical reactions, thus representing an overall formal process to access carbyne equivalents. The authors of this communication also noticed the effect of blue light on aryldiazoacetates 1, but did not synthetically exploit this to any signicant extent. In recent years, the chemistry of donor/acceptor metal carbenes has been broadly developed for synthesis. These intermediates, typically prepared from aryldiazoacetates or vinyldiazoacetates, have attenuated reactivity compared to metal carbenes lacking a donor group. Donor/acceptor carbenes derived from the thermal decomposition of aryldiazoacetates have been shown to undergo relatively selective cyclopropanations, N–H and C–H insertions. |
| Starting Page | 5112 |
| Ending Page | 5118 |
| Page Count | 7 |
| File Format | PDF HTM / HTML |
| PubMed reference number | 29938043 |
| Volume Number | 9 |
| Alternate Webpage(s) | https://open.library.emory.edu/publications/emory:t0jw2/pdf/ |
| Alternate Webpage(s) | https://pubs.rsc.org/en/content/articlepdf/2018/sc/c8sc01165f |
| Journal | Chemical Science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
