The present invention relates to a method for producing (functionalized) biaryls by employing a visible-light-driven, gold-catalyzed CC cross-coupling reaction system involving boron- and silicon-containing aryl compounds and aryldiazonium compounds. Moreover, the present invention relates to the use of such boron- and silicon-containing aryl compounds and aryldiazonium compounds, as well as related gold catalysts, in the manufacture of (functionalized) biaryls.

The present invention relates to a method for producing (functionalized) biaryls by employing a visible-light-driven, gold-catalyzed CC cross-coupling reaction system involving boron- and silicon-containing aryl compounds and aryldiazonium compounds. Moreover, the present invention relates to the use of such boron- and silicon-containing aryl compounds and aryldiazonium compounds, as well as related gold catalysts, in the manufacture of (functionalized) biaryls.

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

Disclosed is a f fluorination method comprising providing a fluorinating reagent and a solvent to a reaction mixture; providing a compound having the formula ArX to the reaction mixture; wherein, A is a aryl, substituted aryl, heteroaryl or substituted heteroaryl, and X is CI, Br, I or NO.sub.2, providing tetramethylammonium 2,6-dimethylphenolate to the reaction mixture; and reacting under conditions sufficient to provide a species having the formula ArF.

Disclosed is a f fluorination method comprising providing a fluorinating reagent and a solvent to a reaction mixture; providing a compound having the formula ArX to the reaction mixture; wherein, A is a aryl, substituted aryl, heteroaryl or substituted heteroaryl, and X is CI, Br, I or NO.sub.2, providing tetramethylammonium 2,6-dimethylphenolate to the reaction mixture; and reacting under conditions sufficient to provide a species having the formula ArF.

A solid-supported Pd catalyst is suitable for CC bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a dip catalyst. The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.?1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.?1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

A solid-supported Pd catalyst is suitable for CC bond formation, e.g., via Suzuki-Miyaura and Mizoroki-Heck cross-coupling reactions, with a support that is reusable, cost-efficient, regioselective, and naturally available. Such catalysts may contain Pd nanoparticles on jute plant sticks (GS), i.e., Pd@GS, and may be formed by reducing, e.g., K.sub.2PdCl.sub.4 with NaBH.sub.4 in water, and then used this as a dip catalyst. The dip catalyst can catalyze Suzuki-Miyaura and Mizoroki-Heck cross coupling-reactions in water. The catalysts may have a homogeneous distribution of Pd nanoparticles with average dimensions, e.g., within a range of 7 to 10 nm on the solid support. Suzuki-Miyaura cross-coupling reactions may achieve conversions of, e.g., 97% with TOFs around 4692 h.sup.?1, Mizoroki-Heck reactions with conversions of, e.g., a 98% and TOFs of 237 h.sup.?1, while the same catalyst sample may be used for 7 consecutive cycles, i.e., without addition of any fresh catalyst.

A solid-supported catalyst ligand which chelates palladium (II) species to form a complex that functions as a heterogeneous catalyst that is stable and can be recycled without significantly losing any catalytic activity in a variety of chemical transformations, a method for producing the solid-supported catalyst ligand and a method for catalyzing a palladium cross-coupling reaction, such as the Suzuki-Miyaura, Mizoroki-Heck, and Sonagashira reactions.