91557-32-3Relevant articles and documents
Development of an aryl amination catalyst with broad scope guided by consideration of catalyst stability
McCann, Scott D.,Reichert, Elaine C.,Arrechea, Pedro Luis,Buchwald, Stephen L.
supporting information, p. 15027 - 15037 (2020/10/13)
We have developed a new dialkylbiaryl monophosphine ligand, GPhos, that supports a palladium catalyst capable of promoting carbon-nitrogen cross-coupling reactions between a variety of primary amines and aryl halides; in many cases, these reactions can be carried out at room temperature. The reaction development was guided by the idea that the productivity of catalysts employing BrettPhos-like ligands is limited by their lack of stability at room temperature. Specifically, it was hypothesized that primary amine and N-heteroaromatic substrates can displace the phosphine ligand, leading to the formation of catalytically dormant palladium complexes that reactivate only upon heating. This notion was supported by the synthesis and kinetic study of a putative off-cycle Pd complex. Consideration of this off-cycle species, together with the identification of substrate classes that are not effectively coupled at room temperature using previous catalysts, led to the design of a new dialkylbiaryl monophosphine ligand. An Ot-Bu substituent was added ortho to the dialkylphosphino group of the ligand framework to improve the stability of the most active catalyst conformer. To offset the increased size of this substituent, we also removed the para i-Pr group of the non-phosphorus-containing ring, which allowed the catalyst to accommodate binding of even very large α-tertiary primary amine nucleophiles. In comparison to previous catalysts, the GPhos-supported catalyst exhibits better reactivity both under ambient conditions and at elevated temperatures. Its use allows for the coupling of a range of amine nucleophiles, including (1) unhindered, (2) five-membered-ring N-heterocycle-containing, and (3) α-tertiary primary amines, each of which previously required a different catalyst to achieve optimal results.
Phenylamidine and phenylguanidine derivatives and their use as antidiabetic agents
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, (2008/06/13)
Compounds of formula I STR1 and their salts in which n=0 or 1, R1 and R2 are each aliphatic or cycloalkyl or NR1 R2 is an optionally substituted heterocyclic ring, R3 is alkyl, cycloalkyl or optionally substituted amino, R5 is an aliphatic group, R6 is H, an optionally substituted aliphatic group or a cycloalkyl group, or R3 and R5 together with the nitrogen and carbon atoms to which they are attached form an optionally substituted heterocyclic ring or R5 and R6 together with the nitrogen to which they are attached form a heterocyclic ring optionally substituted by alkyl and R7 is optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, trifluoromethyl or cyano have utility as hypoglycemic agents.
