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- Di Tommaso, Ester Maria, et al.
(författare)
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Ortho-Functionalization of Azobenzenes via Hypervalent Iodine Reagents
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Annan publikation (övrigt vetenskapligt/konstnärligt)abstract
- Ortho-functionalized azobenzenes are much sought-after molecular switches. They may be tuned to absorb in the visible range of light and in many cases, the Z-isomers have very high thermal half-lives. However, methods to introduce substituents in ortho-position are still rare. This work presents the synthesis of azobenzenes with an iodine(III) moiety in the ortho-position. This novel class of diaryliodonium salts is demonstrated to efficiently arylate oxygen, nitrogen, carbon and sulfur nucleophiles under metal-free conditions. Selective transfer of the azobenzene moiety to the nucleophile gives access to an unprecedented range of ortho-substituted azobenzenes. In addition, the structure of these versatile reagents has been analyzed by X-ray crystallography and their photo-switching properties were investigated by NMR and UV-vis spectroscopy.
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- Kumar, Bhaskar Pal, et al.
(författare)
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Photoredox-Catalyzed Stereoselective Vinylation Reactions with Vinylbenziodoxol(on)es
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Annan publikation (övrigt vetenskapligt/konstnärligt)abstract
- We have disclosed an efficient transition-metal-free radical-mediated C-C cross-coupling reaction of 4-alkyl-1,4-DHPs and VBXs through photo-redox catalysis to afford vinylated products in good yields with retention of configuration from parent VBXs. This mild photocatalysis system featured excellent functional group tolerance, a wide range of substrate scope and unique stereoselectivities. The utility of this new protocol has been demonstrated via the syntheses of diastereoselective C-vinyl glycosides. Preliminary mechanistic studies signify the involvement of radicals and the formation of ligand coupled TS in the reaction pathway.
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- Villo, Piret, et al.
(författare)
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Inside front cover
- 2018
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Annan publikation (övrigt vetenskapligt/konstnärligt)
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