24021-55-4Relevant academic research and scientific papers
Deaminative Arylation of Amino Acid-derived Pyridinium Salts
Hoerrner, Megan E.,Baker, Kristen M.,Basch, Corey H.,Bampo, Earl M.,Watson, Mary P.
supporting information, p. 7356 - 7360 (2019/09/30)
A Suzuki-Miyaura cross-coupling of α-pyridinium esters and arylboroxines has been developed. Combined with formation of the pyridinium salts from amino acid derivatives, this method enables amino acid derivatives to be efficiently transformed into α-aryl
Palladium-Catalyzed α-Arylation of Carboxylic Acids and Secondary Amides via a Traceless Protecting Strategy
He, Zhi-Tao,Hartwig, John F.
supporting information, p. 11749 - 11753 (2019/08/26)
A novel traceless protecting strategy is presented for the long-standing challenge of conducting the palladium-catalyzed α-arylation of carboxylic aids and secondary amides with aryl halides. Both of the presented coupling processes occur with a variety of carboxylic acids and amides and with a variety of aryl bromides containing a broad range of functional groups, including base-sensitive functionality like acyl, alkoxycarbonyl, nitro, cyano, and even hydroxyl groups. Five commercial drugs were prepared through this method in one step in 81-96% yield. Gram-scale synthesis of medication Naproxen and Flurbiprofen with low palladium loading further highlights the practical value of this method.
Construction of a visible light-driven hydrocarboxylation cycle of alkenes by the combined use of Rh(i) and photoredox catalysts
Murata, Kei,Numasawa, Nobutsugu,Shimomaki, Katsuya,Takaya, Jun,Iwasawa, Nobuharu
supporting information, p. 3098 - 3101 (2017/03/17)
A visible light driven catalytic cycle for hydrocarboxylation of alkenes with CO2 was established using a combination of a Rh(i) complex as a carboxylation catalyst and [Ru(bpy)3]2+ (bpy = 2,2′- bipyridyl) as a photoredox catalyst. Two key steps, the generation of Rh(i) hydride species and nucleophilic addition of π-benzyl Rh(i) species to CO2, were found to be mediated by light.
Nickel-catalyzed reductive carboxylation of styrenes using CO2
Williams, Catherine M.,Johnson, Jeffrey B.,Rovis, Tomislav
supporting information; experimental part, p. 14936 - 14937 (2009/03/12)
A nickel-catalyzed reductive carboxylation of styrenes using CO2 has been developed. The reaction proceeds under mild conditions using diethylzinc as the reductant. Preliminary data suggests the mechanism involves two discrete nickel-mediated catalytic cycles, the first involving a catalyzed hydrozincation of the alkene followed by a second, slower nickel-catalyzed carboxylation of the in situ formed organozinc reagent. Importantly, the catalyst system is very robust and will fixate CO2 in good yield even if exposed to only an equimolar amount introduced into the headspace above the reaction. Copyright
