Recent Advances in Pd-Catalyzed Reactions Involving the “On-Water” Mechanism  

作　　者：Dong Wei Guo-Qiang Lin 

机构地区：[1]State Key Laboratory of Systems Medicine for Cancer,Shanghai Cancer Institute,Shanghai Key Laboratory of Systems Regulation and Clinical Translation for Cancer,Ren Ji Hospital,Shanghai Jiao Tong University School of Medicine,Shanghai,200127 China [2]State Key Laboratory of Chemical Biology,Shanghai Institute of Organic Chemistry,University of Chinese Academy of Sciences,Chinese Academy of Sciences,Shanghai,200032 China

出　　处：《Chinese Journal of Chemistry》2024年第5期533-542,共10页中国化学（英文版）

基　　金：support from the National Natural Science Foundation of China(22101296);the State Key Laboratory of Systems Medicine for Cancer(SB23-09,KF2130-93).

摘　　要：As the chemical industry grapples with the need for more eco-friendly practices,the use of water as a reaction medium is gaining attraction in organic transformations.This mini-review delves into Pd-catalyzed reactions that utilize the "on-water" mechanism,spanning from 2019 to late 2023.These reactions are neatly categorized into several types: (A) Catalytic C—H activations,(B) Mizoroki- Heck-type reactions,(C) Suzuki-Miyaura reactions,and (D) Cyclization reactions.By showcasing the potential of water as a sustainable reaction medium for organic transformations,these reactions leave no doubt about the importance of embracing eco-friendly practices in the chemical industry.Key Scientists In 1980,a seminal work by Breslow et al.showed an acceleration of reaction rate in the Diels-Alder reaction.Sharpless and co-workers noted a significant increase in the rate of the [2σ+2σ+2π] cycloaddition of quadricyclane and dimethyl azodicarboxylate (DMAD) when the reaction was conducted in water,as opposed to when it was carried out in organic solvents.The term "on-water" was then coined to describe this phenomenon.This strategy was further expanded to transition-metal catalyzed transformations by Ackermann in 2011.Later,Varma and Leazer disclosed a Pd-catalyzed Mizoroki-Heck type arylation of alkenes with diaryliodonium salts “on-water”.The enantioselective version of "on-water" process was not realized until 2014 by the Zhou group.Later on,the Schaub group described a Pd-catalyzed Suzuki–Miyaura coupling reaction of electron-poor aryl chlorides with water,using only 50 ppm of catalyst loading.Very recently,Liu and Lin extended the "on-water" strategy to Pd-catalyzed double Mizoroki-Heck reactions.This mini-review has focused on Pd-catalyzed reactions involving the “on-water” mechanism.

关 键 词：PD-CATALYZED “On-water” Green chemistry Aqueous reactions Mechanism Methodology and reactions Mizoroki-Heck reaction CROSS-COUPLING 

分 类 号：O62[理学—有机化学]