92022-07-6Relevant academic research and scientific papers
Benzylic C?H Functionalisation by [Et3SiH+KOtBu] leads to Radical Rearrangements in o-tolyl Aryl Ethers, Amines and Sulfides
Arokianathar, Jude N.,Kolodziejczak, Krystian,Bugden, Frances E.,Clark, Kenneth F.,Tuttle, Tell,Murphy, John A.
supporting information, p. 2260 - 2267 (2020/05/06)
Reaction of Et3SiH+KOtBu with diaryl ethers, sulfides and amines that feature an ortho alkyl group leads to rearrangement products. The rearrangements arise from formation of benzyl radicals, likely formed through hydrogen atom abstraction by triethylsilyl radicals. The rearrangements involve cyclisation of the benzyl radical onto the partner arene, which, from computation, is the rate determining step. In the case of diaryl ethers, Truce-Smiles rearrangements arise from radical cyclisations to form 5-membered rings, but for diarylamines, cyclisations to form dihydroacridines are observed. (Figure presented.).
Copper-catalyzed recycling of halogen activating groups via 1,3-halogen migration
Grigg, R. David,Van Hoveln, Ryan,Schomaker, Jennifer M.
supporting information, p. 16131 - 16134,4 (2020/09/09)
A Cu(I)-catalyzed 1,3-halogen migration reaction effectively recycles an activating group by transferring bromine or iodine from a sp2 to a benzylic carbon with concomitant borylation of the Ar-X bond. The resulting benzyl halide can be reacted in the same vessel under a variety of conditions to form an additional carbon-heteroatom bond. Cross-over experiments using an isotopically enriched bromide source support intramolecular transfer of Br. The reaction is postulated to proceed via a Markovnikov hydrocupration of the o-halostyrene, oxidative addition of the resulting Cu(I) complex into the Ar-X bond, reductive elimination of the new sp3 C-X bond, and final borylation of an Ar-Cu(I) species to turn over the catalytic cycle.
The synthesis of novel photochromic diarylethenes bearing a biphenyl moiety and the effects of substitution on their properties
Pu, Shouzhi,Miao, Wenjuan,Cui, Shiqiang,Liu, Gang,Liu, Weijun
experimental part, p. 257 - 267 (2010/09/09)
A new class of diarylethene bearing a biphenyl moiety was synthesized and the effects of substitution on photochromism, fluorescence and electrochemical character, were investigated. Under alternating irradiation with UV and visible light, the compounds exhibited good photochromism and functioned as?fluorescent photoswitches both in solution and in PMMA film. Electron-donating substituents shifted the λmax of the diarylethenes to longer wavelengths and decreased their cyclization quantum yield, while electron-withdrawing substituents greatly increased both cyclization and cycloreversion quantum yield. In addition, cyclic voltammetry revealed that the substituents had a significant effect on the electrochemical behaviour of the diarylethene derivatives.
Synthesis of Sugar-containing Polymers by Self-condensation with Diboronic Acid
Mikami, Masafumi,Shinkai, Seiji
, p. 153 - 154 (2007/10/02)
Self-condensation of 3,3'-bis(N,N-di-n-butylaminomethyl)biphenyl-4,4'-diboronic acid and saccharides yields polymers containing saccharides in the main chain: they show unique CD spectroscopic porperties which reflect the chirality of saccharides.
