Journal
TETRAHEDRON
Volume 72, Issue 48, Pages 7826-7831Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.07.069
Keywords
Photochemistry; Diazines; Radical chemistry; Photo-Arbuzov reaction; Diazinyl phosphonate
Categories
Funding
- la Fondation pour l'ENSCMu
- IUF
- Actelion
- COST Action [CM1201]
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Under mild UVA irradiation, the C-Br bond of bromodiazines can be activated to generate the corresponding radical intermediate. In the presence of alkynes, alkenylation reactions occurred to afford vinyl pyrimidine in moderate yields. Csp2-phosphorous bond can also be easily created in a photochemical version of the Arbuzov reaction. With UVA and a stoichiometric amount of trimethyl phosphite, the corresponding phosphonates were isolated in good to high yields. Very interesting selectivities were observed under these mild irradiation conditions. Functionalized substrates can be engaged and the resulting products could be further derivatized. (C) 2016 Elsevier Ltd. All rights reserved.
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