A novel visible-light-induced palladium-catalyzed Heck reaction for bromine sugars and aryl olefins with high regio- and stereochemistry selectivity for the preparation of glycosyl styrene is described. This reaction takes place in one step at room temperature by using a simple and readily available starting material. This protocol can be scaled up to a wide range of glycosyl bromide donors and aryl olefin substrates. Mechanistic studies indicate that a radical addition pathway is involved.
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http://dx.doi.org/10.1021/acs.orglett.0c02053 | DOI Listing |
Org Lett
June 2024
Henan University of Chinese Medicine, Zhengzhou 450046, China.
The hybrid nature of Pd(I)-alkyl radical species has enabled a wide array of radical-based transformations. However, in this transformation, the secondary Pd(I)-alkyl radical species are prone to recombining into Pd(II)-alkyl species to give Heck-type products via β-H loss. Herein, we report a visible-light-induced, three-component Pd-catalyzed 1,2-aminoalkylation of alkenes with readily available alkyl halides and amines to construct C-C and C-N bonds simultaneously.
View Article and Find Full Text PDFChemistry
May 2024
Institute of Inorganic Chemistry I, Ulm University, Albert-Einstein-Allee 11, 89081, Ulm, Germany.
Visible light-induced charge separation and directional charge transfer are cornerstones for artificial photosynthesis and the generation of solar fuels. Here, we report synthetic access to a series of noble metal-free donor-acceptor dyads based on bodipy light-absorbers and redox-active quinone/anthraquinone charge storage sites. Peripheral functionalization of the quinone/anthraquinone units with alkynes primes the dyads for integration into a range of light-harvesting systems, e.
View Article and Find Full Text PDFJ Am Chem Soc
November 2022
Department of Chemistry, University of California, Berkeley, California 94720, United States.
Chemical synthesis of natural products is typically inspired by the structure and function of a target molecule. When both factors are of interest, such as in the case of taxane diterpenoids, a synthesis can both serve as a platform for synthetic strategy development and enable new biological exploration. Guided by this paradigm, we present here a unified enantiospecific approach to diverse taxane cores from the feedstock monoterpenoid ()-carvone.
View Article and Find Full Text PDFJ Am Chem Soc
October 2022
Department of Chemistry, Tokyo Institute of Technology, O̅okayama, Meguro-ku, Tokyo 152-8551, Japan.
Despite the recent tremendous progress on transition-metal/photoredox dual catalysis in organic synthesis, single transition-metal catalysis under visible-light irradiation, which can utilize light energy more efficiently, is still underdeveloped. Herein, we report the design of photosensitizing phosphinoacridine bidentate ligands for visible-light-induced transition-metal catalysis, expecting that the electron-accepting acridine moiety would create a highly reactive electron-deficient metal center toward reductive elimination via metal-to-ligand charge transfer (MLCT). Using these ligands, we have achieved a palladium-catalyzed cross-coupling reaction of aryl halides with carboxylic acids under visible-light irradiation.
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