221024-35-7Relevant academic research and scientific papers
Deoxygenative Deuteration of Carboxylic Acids with D2O
Zhang, Muliang,Yuan, Xiang-Ai,Zhu, Chengjian,Xie, Jin
, p. 312 - 316 (2019)
We report a general, practical, and scalable means of preparing deuterated aldehydes from aromatic and aliphatic carboxylic acids with D2O as an inexpensive deuterium source. The use of Ph3P as an O-atom transfer reagent can facilitate the deoxygenation of aromatic acids, while Ph2POEt is a better O-atom transfer reagent for aliphatic acids. The highly precise deoxygenation of complex carboxylic acids makes this protocol promising for late-stage deoxygenative deuteration of natural product derivatives and pharmaceutical compounds.
Decarbonylative Suzuki-Miyaura Cross-Coupling of Aroyl Chlorides
Zhou, Tongliang,Xie, Pei-Pei,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
supporting information, p. 6434 - 6440 (2020/09/02)
Herein, we report a catalyst system for Pd-catalyzed decarbonylative Suzuki-Miyaura cross-coupling of aroyl chlorides with boronic acids to furnish biaryls. This strategy is suitable for a broad range of common aroyl chlorides and boronic acids. The synthetic utility is highlighted in the direct late-stage functionalization of pharmaceuticals and natural products capitalizing on the presence of carboxylic acid moiety. Extensive mechanistic and DFT studies provide key insight into the reaction mechanism and high decarbonylative cross-coupling selectivity.
Synthesis and structure of poly(N-propargylbenzamides) bearing chiral ester groups
Tabei, Junichi,Nomura, Ryoji,Masuda, Toshio
, p. 573 - 577 (2007/10/03)
N-Propargylbenzamides having chiral ester groups on the benzene ring, 1-6, were polymerized with (nbd)Rh+[n6-C6H5-(C6 H5)3] to afford soluble polymers with moderate molecular weights (Mn = 34 000-100 000) in good yield. The 1H NMR spectra demonstrated that the polymers have stereoregular structures (cis = 91-100%). The influence of the substitution position for the chiral ester group on the secondary structure was examined. From the comparison of the CD effects of poly(1)-poly(3), the meta-substituted polymer was proven to possess a one-handed helical conformation. When the chiral center was closer to the benzene ring or chiral ester group was bulkier, the polymers showed more intense chiroptical properties. A variable temperature CD spectroscopic study showed that the helical structure of poly(2) and poly(6) was thermally stable. However, the CD spectra of poly(4) and poly(5) were inverted in sign on temperature change in chloroform or toluene, meaning that the helix inversion took place. The temperature of helix inversion could be controlled by copolymerizing with N-propargyl-benzamide (7).
