117635-43-5Relevant articles and documents
Nickel- vs Palladium-Catalyzed Synthesis of Protected Phenols from Aryl Halides
Mann, Grace,Hartwig, John F.
, p. 5413 - 5418 (1997)
We report the nickel-catalyzed formation of alkyl and silyl ethers from aryl halides in one step. These ethers can act as precursors to phenols by reaction with Bronsted or Lewis acids or with fluoride. A combination of Ni(COD)2 and DPPF mediates the formation of tert-butyl aryl, methyl aryl, and tert-butyldimethyl silyl aryl ethers efficiently from aryl halides and sodium alkoxides or sodium siloxides under mild reaction conditions. Reactions to form the tert-butyl aryl ethers mediated by nickel complexes have lower turnover numbers than the analogous palladium-catalyzed reactions. However, reactions to form methyl aryl ethers show higher yields when catalyzed by a combination of Ni(COD)2 and BINAP than when catalyzed by BINAP or DPPF and palladium catalyst precursors. Similarly, the formation of silyl aryl ethers occurs in higher yields and under milder conditions when catalyzed by a combination Ni(COD)2 and DPPF than when catalyzed by palladium complexes. We also report improved yields from our previous results for the palladium-catalyzed conversion of aryl halides to tert-butyl aryl ethers.
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
, p. 19257 - 19262 (2019/12/02)
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Selective Activation of Human Caseinolytic Protease P (ClpP)
Stahl, Matthias,Korotkov, Vadim S.,Balogh, Dóra,Kick, Leonhard M.,Gersch, Malte,Pahl, Axel,Kielkowski, Pavel,Richter, Klaus,Schneider, Sabine,Sieber, Stephan A.
supporting information, p. 14602 - 14607 (2018/09/25)
Caseinolytic protease P (ClpP) is the proteolytic component of the ClpXP protein degradation complex. Eukaryotic ClpP was recently found to act within the mitochondria-specific unfolded protein response (UPRmt). However, its detailed function a
