68294-33-7Relevant articles and documents
Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage
Ma, Yangmin,Shao, Lei,Szostak, Michal,Wang, Ruihong,Zhang, Jin,Zhang, Pei
supporting information, (2022/01/04)
Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe
Direct suzuki-miyaura coupling with naphthalene-1,8-diaminato (dan)-substituted organoborons
Yoshida, Hiroto,Seki, Michinari,Kamio, Shintaro,Tanaka, Hideya,Izumi, Yuki,Li, Jialun,Osaka, Itaru,Abe, Manabu,Andoh, Hiroki,Yajima, Tomoki,Tani, Tomohiro,Tsuchimoto, Teruhisa
, p. 346 - 351 (2019/12/24)
The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)2 in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R-B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.
Cross-Coupling of Aryl Trifluoromethyl Sulfones with Arylboronates by Cooperative Palladium/Rhodium Catalysis
Fukuda, Jun-Ichi,Nogi, Keisuke,Yorimitsu, Hideki
supporting information, p. 8987 - 8991 (2019/11/11)
The Suzuki-Miyaura arylation of aryl trifluoromethyl sulfones via C-SO2 bond cleavage has been developed by means of cooperative palladium/rhodium catalysis. A series of aryl trifluoromethyl sulfones and arylboronic acid neopentylglycol esters are converted to the corresponding biaryls. Mechanistic investigations suggest that (1) the rhodium catalyst mediates the transfer of the aryl ring from arylboronate to palladium, resulting in the acceleration of the transmetalation step, and (2) the C-C bond-forming reductive elimination step is the turnover-limiting step.