1395071-71-2Relevant articles and documents
Pd- And Ni-Based Systems for the Catalytic Borylation of Aryl (Pseudo)halides with B2(OH)4
Munteanu, Charissa,Spiller, Taylor E.,Qiu, Jun,Delmonte, Albert J.,Wisniewski, Steven R.,Simmons, Eric M.,Frantz, Doug E.
, p. 10334 - 10349 (2020/09/18)
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.
Furazan-containing bromoarenes in the Suzuki-Miyaura reaction
Vasil'ev,Struchkova,Sheremetev,Levinson,Varganov,Lyssenko
, p. 2306 - 2314 (2012/10/30)
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.
