20938-43-6Relevant articles and documents
Tezuka,Miller
, p. 4201,4205, 4206 (1978)
Copper-catalysed low-temperature water-gas shift reaction for selective deuteration of aryl halides
Bartling, Stephan,Beller, Matthias,Bourriquen, Florian,Junge, Kathrin,Li, Wu,Liu, Weiping,Qu, Ruiyang,Rockstroh, Nils
, p. 14033 - 14038 (2021/11/12)
The introduction of deuterium atoms into organic compounds is of importance for basic chemistry, material sciences, and the development of drugs in the pharmaceutical industry, specifically for identification and quantification of metabolites. Hence, methodologies for the synthesis of selectively labelled compounds continue to be a major area of interest for many scientists. Herein, we present a practical and stable heterogeneous copper catalyst, which permits for dehalogenative deuterationviawater-gas shift reaction at comparably low temperature. This novel approach allows deuteration of diverse (hetero)aryl halides with good functional group tolerance, and no reduction of the aromatic rings or other easily reducible formyl and cyano groups. Multi-gram experiments show the potential of this method in organic synthesis and medicinal chemistry.
Pt-Pd nanoalloy for the unprecedented activation of carbon-fluorine bond at low temperature
Dhital, Raghu Nath,Ehara, Masahiro,Haesuwannakij, Setsiri,Nomura, Keigo,Sakurai, Hidehiro,Sato, Yoshinori
, p. 1180 - 1185 (2020/10/18)
Carbon-fluorine bonds are considered the most inert organic functionality and their selective transformation under mild conditions remains challenging. Herein, we report a highly active Pt-Pd nanoalloy as a robust catalyst for the transformation of C-F bonds into C-H bonds at low temperature, a reaction that has hitherto often required harsh conditions. The alloying of Pt with Pd is crucial to promote the overall C-F bond. DFT calculations elucidated that the key step is the selective oxidative addition of the O-H bond of 2-propanol to a Pd center prior to C-F bond activation at a Pt site, which crucially reduces the activation energy of the C-F bond cleavage. Therefore, both Pt and Pd work independently but synergistically to promote the overall reaction.