A General Method for the Suzuki−Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides:  Synthesis of Di- and Tri-ortho-substituted Biaryls in 2-Propanol at Room Temperature

A general method for the <i>N</i>-arylation of sulfamides with aryl bromides is described. The protocol leverates a dual-catalytic system of nickel and a photoexcitable iridium complex and proceeds at room temperature under visible light irradiation. Using these tactics, aryl boronic esters and aryl chlorides can be carried through the reaction untouched. Thereby, this method complements known Buchwald-Hartwig coupling methods for N-arylation of sulfamides.

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Room temperature Stille cross-coupling reaction of unreactive aryl chlorides and heteroaryl chlorides

Chemical Communications ◽

10.1039/b917711f ◽

2010 ◽

Vol 46 (3) ◽

pp. 478-480 ◽

Cited By ~ 33

Author(s):

Dong-Hwan Lee ◽

Abu Taher ◽

Wha-Seung Ahn ◽

Myung-Jong Jin

Keyword(s):

Room Temperature ◽

Coupling Reaction ◽

Cross Coupling ◽

Aryl Chlorides ◽

Cross Coupling Reaction

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ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.

ChemInform ◽

10.1002/chin.200949085 ◽

2009 ◽

Vol 40 (49) ◽

Author(s):

Zhong Jin ◽

Su-Xian Guo ◽

Xiao-Peng Gu ◽

Ling-Ling Qiu ◽

Hai-Bing Song ◽

...

Keyword(s):

Room Temperature ◽

Cross Coupling ◽

Palladium Chloride ◽

Coupling Reactions ◽

Chloride Complexes ◽

Aryl Chlorides ◽

Arylboronic Acids ◽

Cross Coupling Reactions ◽

Highly Active ◽

Palladium Chloride Complexes

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A General Method for the Suzuki−Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides: Synthesis of Di- and Tri-ortho-substituted Biaryls in 2-Propanol at Room Temperature

A General Method for the Suzuki—Miyaura Cross-Coupling of Sterically Hindered Aryl Chlorides: Synthesis of Di- and Tri-ortho-substituted Biaryls in 2-Propanol at Room Temperature.

An N-Heterocyclic Carbene Ligand with Flexible Steric Bulk Allows Suzuki Cross-Coupling of Sterically Hindered Aryl Chlorides at Room Temperature

An N-Heterocyclic Carbene Ligand with Flexible Steric Bulk Allows Suzuki Cross-Coupling of Sterically Hindered Aryl Chlorides at Room Temperature.

NHC-Pd(II)-azole complexes catalyzed Suzuki–Miyaura cross-coupling of sterically hindered aryl chlorides with arylboronic acids

Highly Active Palladium Catalysts Supported by Bulky Proazaphosphatrane Ligands for Stille Cross-Coupling: Coupling of Aryl and Vinyl Chlorides, Room Temperature Coupling of Aryl Bromides, Coupling of Aryl Triflates, and Synthesis of Sterically Hindered Biaryls

Triphenylphosphine as a Ligand for Room-Temperature Ni(0)-Catalyzed Cross-Coupling Reactions of Aryl Chlorides with Arylboronic Acids

Macromolecular Effect: Synthesis of a Ferrocenylmethylphosphine-Containing Polymer as Highly Efficient Ligands for Room-Temperature Palladium(0)-Catalyzed Suzuki Cross-Coupling Reactions of Aryl Chlorides

Photochemically-Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides

Room temperature Stille cross-coupling reaction of unreactive aryl chlorides and heteroaryl chlorides

ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.

ChemInform Abstract: Highly Active, Well-Defined (Cyclopentadiene)(N-heterocyclic carbene)palladium Chloride Complexes for Room-Temperature SuzukiâMiyaura and BuchwaldâHartwig Cross-Coupling Reactions of Aryl Chlorides and Deboronation Homocoupling of Arylboronic Acids.