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Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 696-62-8 para-iodoanisole 
• 36387-84-5 4-bromo-9-oxido-8-oxa-7,9-diazabicyclo[4.3.0]nona-1⁽⁹⁾,2,4,6-tetraene 
• 5228-61-5 5-bromo-2-nitroaniline 
• 875-51-4 4-Bromo-2-nitroaniline 
• 51376-06-8 5-bromo-benzo[1,2,5]oxadiazole 
• 5720-07-0 4-methoxyphenylboronic acid 

Relevant academic research and scientific papers

Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4

Despite recent advancements in metal-catalyzed borylations of aryl (pseudo)halides, there is a continuing need to develop robust methods to access both early-stage and late-stage organoboron intermediates amendable for further functionalization. In particular, the development of general catalytic systems that operate under mild reaction conditions across a broad range of electrophilic partners remains elusive. Herein, we report the development and application of three catalytic systems (two Pd-based and one Ni-based) for the direct borylation of aryl (pseudo)halides using tetrahydroxydiboron (B2(OH)4). For the Pd-based catalyst systems, we have identified general reaction conditions that allow for the sequestration of halide ions through simple precipitation that results in catalyst loadings as low as 0.01 mol % (100 ppm) and reaction temperatures as low as room temperature. We also describe a complementary Ni-based catalyst system that employs simple unligated Ni(II) salts as an inexpensive alternative to the Pd-based systems for the borylation of aryl (pseudo)halides. Extrapolation of all three systems to a one-pot tandem borylation/Suzuki-Miyaura cross-coupling is also demonstrated on advanced intermediates and drug substances.

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

Furazan-containing bromoarenes in the Suzuki-Miyaura reaction

The palladium-catalyzed cross-coupling reactions of 3-[bromo(het)aryl] furazans and bromobenzofurazans with arylboronic acids afford target biaryls in good yields. 3-Bromo-4-phenylfurazan containing a bromine atom in the furazan ring undergoes decomposition under the reaction conditions.