Synthesis of 3-trifluoromethylated 1,3-butadienes via a Pd(0)-catalyzed fluorinated Heck reaction

文献情報

出版日 2020-03-25

DOI 10.1039/D0RE00093K

インパクトファクター 4.239

著者

Yang Li, Meng Hao, Ming Xia, Ning Sun, Cai-Lin Zhang, Wen-Qing Zhu

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要旨

1,3-Butadienes play a key role in modern synthetic chemistry and biochemistry because they are well-known precursors for the synthesis of retinoids. A new and efficient synthesis of 3-trifluoromethylated 1,3-butadienes via a Pd(0)-catalyzed fluorinated Heck reaction is described. Without an additive, the reaction of 2-bromo-3,3,3-trifluoropropene, an abundant and ozone friendly CF3 building block, with acrylamides afforded 3-trifluoromethylated 1,3-butadienes in good to excellent yields with high regioselectivity and s-trans/s-cis ratios under mild conditions. Inspired by the concept of space–time yield for continuous reactions, the average space–time yield calculated shows that all the reactions far exceed 1 g gcat−1 h−1, which is high enough for further scale-up, suggesting that small amounts of catalyst and a very small reactor are required.

掲載誌

Reaction Chemistry & Engineering

CiteScore: 0

自己引用率: 8.8%

年間論文数: 284

Reaction Chemistry & Engineering is an interdisciplinary journal reporting cutting-edge research focused on enhancing the understanding and efficiency of reactions. Reaction engineering leverages the interface where fundamental molecular chemistry meets chemical engineering and technology. Challenges in chemistry can be overcome by the application of new technologies, while engineers may find improved solutions for process development from the latest developments in reaction chemistry. Reaction Chemistry & Engineering is a unique forum for researchers whose interests span the broad areas of chemical engineering and chemical sciences to come together in solving problems of importance to wider society. All papers should be written to be approachable by readers across the engineering and chemical sciences. Papers that consider multiple scales, from the laboratory up to and including plant scale, are particularly encouraged.