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Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation
Abstract
Secondary Selectivity: Organic molecules consist principally of rings and chains of methylene (secondary) CH 2 groups, intermittently adorned with oxygen or nitrogen centers and more heavily substituted carbons at the junctions. Synthetic transformations would be most efficient if the C–H bonds in any particular methylene group along the framework could be targeted for selective modification. However, for the most part, these carbon centers prove remarkably hard to differentiate for reactive purposes. Chen and White (p. 566 ) now show that an iron catalyst can direct peroxide to oxidize specific secondary C–H bonds preferentially, and with reasonable efficiency, in a range of complex molecules. The observed selectivities follow predictable trends correlated with the electronic and steric environment of the target site.
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Cited by
Synthetic Applications of Proton-Coupled Electron Transfer
Gentry, E. C., & Knowles, R. R. (2016) · Accounts of Chemical Research · doi:10.1021/acs.accounts.6b00272 · Cited by 773
O–H hydrogen bonding promotes H-atom transfer from α C–H bonds for C-alkylation of alcohols
Jeffrey, J. L., Terrett, J. A., & MacMillan, D. W. C. (2015) · Science · doi:10.1126/science.aac8555 · Cited by 594
Dai, Y., Poidevin, C., Ochoa‐Hernández, C., Auer, A. A., & Tüysüz, H. (2020) · Angewandte Chemie International Edition · doi:10.1002/anie.201915034 · Cited by 269
Chemo- and site-selective derivatizations of natural products enabling biological studies
Robles, O., & Romo, D. (2014) · Nat. Prod. Rep. · doi:10.1039/c3np70087a · Cited by 154
Metadata
- Authors
- Chen, M. S., & White, M. C.
- Venue
- Science
- Published
- 2010-01-29
- Volume
- 327
- Issue
- 5965
- Pages
- 566-571
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2019406135
- Cited by
- 765
- References
- 0
- FWCI
- 37.27
- Type
- journal article
- Language
- en
- Open access
- closed
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