138371-54-7Relevant academic research and scientific papers
Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N-C Cleavage of Imides
Amani, Javad,Alam, Rauful,Badir, Shorouk,Molander, Gary A.
, p. 2426 - 2429 (2017/05/12)
An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N-C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups.
Direct Conversion of Carboxylic Acids to Alkyl Ketones
Amani, Javad,Molander, Gary A.
, p. 3612 - 3615 (2017/07/15)
An efficient and mild method for acyl-Csp3 bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated c
Fragment Couplings via CO2 Extrusion-Recombination: Expansion of a Classic Bond-Forming Strategy via Metallaphotoredox
Le, C. Chip,MacMillan, David W. C.
supporting information, p. 11938 - 11941 (2015/10/06)
In this study we demonstrate that molecular fragments, which can be readily coupled via a simple, in situ RO-C=OR bond-forming reaction, can subsequently undergo metal insertion-decarboxylation-recombination to generate Csp2-Csp3 bonds when subjected to metallaphotoredox catalysis. In this embodiment the conversion of a wide variety of mixed anhydrides (formed in situ from carboxylic acids and acyl chlorides) to fragment-coupled ketones is accomplished in good to high yield. A three-step synthesis of the medicinal agent edivoxetine is also described using this new decarboxylation-recombination protocol.
