7017-16-5Relevant articles and documents
Synthesis of 4-Trifluoromethylated 1,3-Butadienes via Palladium Catalyzed Heck Reaction
Li, Yang,Hao, Meng,Chang, Yu-Chen,Liu, Yuan,Wang, Wen-Fei,Sun, Ning,Zhu, Wen-Qing,Gao, Ziwei
supporting information, p. 2962 - 2966 (2021/08/23)
1,3-Butadiene plays a key role in modern synthetic chemistry and biochemistry because it is a key intermediate in the synthesis of many drugs. A new and effective method for the synthesis of 4-trifluoromethylated 1,3-butadiene through the fluorinated Heck reaction catalyzed by Pd(0) is described. Without additives, 1-chloro-3,3,3-trifluoropropene (an inexpensive CF3 structural unit that is harmless to ozone) reacts with enamide to synthesize 4-trifluoromethylated 1,3-butadienes with good yield, high regioselectivity and chemical selectivity, and strong tolerance of substrate functional groups such as alkynes, aldehyde, and ester groups.
Rh(i)-Catalyzed regioselective arylcarboxylation of acrylamides with arylboronic acids and CO2
Cai, Lei,Fu, Lei,Gao, Yuzhen,Li, Gang,Li, Shangda,Zhou, Chunlin
supporting information, p. 7328 - 7332 (2020/11/19)
The first Rh(i)-catalyzed regioselective arylcarboxylation of electron-deficient acrylamides with arylboronic acids under atmospheric pressure of CO2 has been developed. A range of acrylamides and arylboronic acids were compatible with this reaction under redox-neutral conditions, leading to a series of malonate derivatives that are versatile building blocks in organic syntheses.
Systematic study of the glutathione (GSH) reactivity of N-arylacrylamides: 1. Effects of aryl substitution
Cee, Victor J.,Volak, Laurie P.,Chen, Yuping,Bartberger, Michael D.,Tegley, Chris,Arvedson, Tara,McCarter, John,Tasker, Andrew S.,Fotsch, Christopher
, p. 9171 - 9178 (2015/12/23)
Success in the design of targeted covalent inhibitors depends in part on a knowledge of the factors influencing electrophile reactivity. In an effort to further develop an understanding of structure-reactivity relationships among N-arylacrylamides, we determined glutathione (GSH) reaction rates for a family of N-arylacrylamides independently substituted at ortho-, meta-, and para-positions with 11 different groups common to inhibitor design. We find that substituent effects on reaction rates show a linear Hammett correlation for ortho-, meta-, and para-substitution. In addition, we note a correlation between 1H and 13C NMR chemical shifts of the acrylamide with GSH reaction rates, suggesting that NMR chemical shifts may be a convenient surrogate measure of relative acrylamide reactivity. Density functional theory calculations reveal a correlation between computed activation parameters and experimentally determined reaction rates, validating the use of such methodology for the screening of synthetic candidates in a prospective fashion.