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Hollow nanoreactors for Pd-catalyzed Suzuki-Miyaura coupling and O-propargyl cleavage reactions in bio-relevant aqueous media.

ABSTRACT: We describe the fabrication of hollow microspheres consisting of mesoporous silica nanoshells decorated with an inner layer of palladium nanoparticles and their use as Pd-nanoreactors in aqueous media. These palladium-equipped capsules can be used to promote the uncaging of propargyl-protected phenols, as well as Suzuki-Miyaura cross-coupling, in water and at physiologically compatible temperatures. Importantly, the depropargylation reaction can be accomplished in a bioorthogonal manner in the presence of relatively high concentrations of biomolecular components and even in the presence of mammalian cells.

SUBMITTER: Destito P

PROVIDER: S-EPMC6419927 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Enhanced aqueous Suzuki-Miyaura coupling allows site-specific polypeptide 18F-labeling.

Project description:The excesses of reagents used in protein chemistry are often incompatible with the reduced or even inverse stoichiometries used for efficient radiolabeling. Analysis and screening of aqueous Pd(0) ligand systems has revealed the importance of a guanidine core and the discovery of 1,1-dimethylguanidine as an enhanced ligand for aqueous Suzuki-Miyaura cross-coupling. This novel Pd catalyst system has now allowed the labeling of small molecules, peptides, and proteins with the fluorine-18 prosthetic [(18)F]4-fluorophenylboronic acid. These findings now enable site-specific protein (18)F-labeling under biologically compatible conditions using a metal-triggered reaction.

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Highly Efficient Method for Suzuki Reactions in Aqueous Media.

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| S-EPMC6641778 | biostudies-literature

Magnetic Lignosulfonate-Supported Pd Complex: Renewable Resource-Derived Catalyst for Aqueous Suzuki-Miyaura Reaction.

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Nickel-catalyzed Suzuki-Miyaura couplings in green solvents.

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Nickel-Catalyzed Suzuki-Miyaura Coupling of Aliphatic Amides.

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| S-EPMC5906067 | biostudies-literature

Nickel-catalyzed Suzuki-Miyaura cross-couplings of aldehydes.

Project description:Transition-metal-catalyzed cross-couplings have been extensively used in the pharmaceutical and agrochemical industries for the construction of diverse C-C bonds. Conventional cross-coupling reactions require reactive electrophilic coupling partners, such as organohalides or sulfonates, which are not environmentally friendly and not naturally abundant. Another disadvantage associated with these transformations is the need for an exogenous base to facilitate the key transmetalation step, and this reagent inevitably induces side reactions and limits the substrate scope. Here, we report an unconventional Suzuki-type approach to the synthesis of biaryls, through nickel-catalyzed deformylative cross coupling of aldehydes with organoboron reagents under base-free conditions. The transformation tolerates structurally diverse (hetero)aryl substituents on both coupling partners and shows high reactivity and excellent functional group tolerance. Furthermore, the protocol was carried out on gram scale and successfully applied to the functionalization of complex biologically active molecules. Mechanistic investigations support a catalytic cycle involving the oxidative addition of the nickel into the aldehyde C(acyl)-H bond with subsequent hydride transfer, transmetalation, decarbonylation and reductive elimination processes.

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