Review
Chemistry, Organic
Xuemei Yin, Shanshan Li, Kun Guo, Lei Song, Xiaoling Wang
Summary: Palladium-catalyzed asymmetric hydrofunctionalization of alkenes is a powerful method to obtain valuable enantioenriched molecules from cheap and readily available feedstocks, but it also faces certain challenges and opportunities.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Chao Xia, Dong-Chao Wang, Gui-Rong Qu, Hai-Ming Guo
Summary: A highly enantioselective allylation reaction of vinylethylene carbonate by asymmetric palladium catalysis has been developed for various N-heteroaromatic substrates. The efficient synthesis of acyclic nucleoside analogs with high yields (up to 96%) and enantioselectivities (up to 99%) was demonstrated with only 0.5 mol% of Pd catalyst. Additionally, these acyclic nucleosides can undergo rapid transformation into a variety of structurally diverse chiral acyclic nucleosides and isonucleosides.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Huanhuan Cui, Changhao Niu, Mimi Xing, Chun Zhang
Summary: A novel NiH-catalyzed highly regioselective coupling of alkenes with vinyl chlorosilanes, constructing C-Si bonds, has been developed. This reaction allows for the synthesis of benzyl organosilanes with various functional groups, which can serve as versatile precursors for preparing complicated organosilicon compounds.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Nuria Vazquez-Galinanes, Isabel Velo-Heleno, Martin Fananas-Mastral
Summary: A method for the use of vinyl epoxides in catalytic allylboration of alkynes is described, which allows for the synthesis of bifunctional skipped dienes bearing both an allylic alcohol and an alkenylboronate from simple starting materials with high regio- and stereoselectivity. These products show versatile reactivity and can be converted into cyclic boron compounds and polyenes.
Article
Chemistry, Applied
Chen Chen, Jie Ding, Liying Liu, Yujie Huang, Bolin Zhu
Summary: The presented palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins utilizes H-phosphinates and secondary phosphine oxides as phosphine sources. Various phosphorylated heteroaromatics are obtained in moderate to good yields with broad functional group compatibility. This protocol enables multiple bond-forming events including C-X (X=O, N, S) and C-P bonds using readily available starting materials, and can be easily applied to large-scale preparation and late-stage functionalization.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Wang Yuchao, Liu Jinbiao, He Zhitao
Summary: This paper summarizes the development, advancements and mechanistic features of palladium-catalyzed asymmetric hydrofunctionalizations of conjugated dienes. Based on the types of allylic stereogenic centers constructed, the review is divided into six parts.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lei Su, Guobin Ma, Yanhong Song, Hegui Gong
Summary: This study demonstrates a facile method for constructing C-3a vinyl substituted hexahydropyrrolidinoindolines based on Ni-catalyzed reductive coupling, showcasing remarkable compatibility with a wide range of alkyl-decorated vinyl triflates, including sterically hindered branched vinyl groups.
Article
Chemistry, Physical
Simon Sieger, Ilja Lubins, Bernhard Breit
Summary: A highly versatile palladium-catalyzed allylation reaction has been reported, providing a waste-free access to allylated nucleophiles with unlimited possibilities for further functionalization. The reaction can be conducted using propadiene in toluene, and the mechanism is supported by deuterium labeling experiments.
Article
Chemistry, Physical
Simon V. Sieger, Ilja Lubins, Bernhard Breit
Summary: A highly versatile palladium-catalyzed allylation reaction using various pronucleophiles has been reported. Through the use of propadiene in toluene, this reaction provides an efficient and waste-free method to obtain allylated nucleophiles with unlimited potential for further functionalization. The Pd/BINAP system is not only capable of adding N-, O-, and S-pronucleophiles, but also C-pronucleophiles to allene. The plausible mechanism is supported by deuterium labeling experiments.
Article
Chemistry, Organic
Du Gao, Zhibin Huang, Guanyu Zhou, Pengcheng Huang, Yanwei Zhao, Yingsheng Zhao
Summary: An undirected ortho-olefination reaction using tri-isobutyl silicon-protected phenol as the substrate, palladium acetate as the catalyst, and inexpensive pyridine derivatives as ligands was reported. The reaction showed good tolerance towards various phenols, providing moderate to good yields. Importantly, bioactive compounds such as hexyl-methoxyphenol and estradiol were successfully synthesized, highlighting the synthetic importance of this method.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Tao Song, Yicong Luo, Kuiyang Wang, Bingyi Wang, Qianjia Yuan, Wanbin Zhang
Summary: This research presents an efficient nickel-catalyzed remote hydroamination and hydroetherification method, which allows the installation of amino or alkoxyl groups at C(sp3)-H positions that are far from the double bond of alkenes. The yields are as high as 93% with exclusive regioselectivities.
Article
Chemistry, Multidisciplinary
Xin Wang, Han-Zhe Miao, Guo-Qiang Lin, Zhi-Tao He
Summary: This study describes feasible protocols to achieve regiodivergent allylic C-H functionalizations via palladium-catalyzed remote substitution, which provides a novel strategy for the seldomly studied migratory Tsuji-Trost reaction. Dictated by a suitable ligand, a process involving 4,3-hydrofunctionalization of the generated conjugated diene intermediate via metal walking is observed with generally >20 : 1 regioselectivity. A major route is also found for 1,4-hydrofunctionalization with a newly synthesized electron-rich bisphosphine ligand.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Li-Guo Lu, Jun-Hua Chen, Xiao-Bo Huang, Miao-Chang Liu, Yun-Bing Zhou, Hua-Yue Wu
Summary: The Pd-catalyzed selective ring opening reaction of cyclopropenones with vinyl epoxides allows for the synthesis of a wide range of conjugated alkadienyl carboxylates in good yield and excellent regioselectivity. This study demonstrates the new application of zwitterionic pi-allyl palladium intermediates in organic synthesis.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Peng Lu, Hongliang Wang, Yihui Mao, Xin Hong, Zhan Lu
Summary: Investigation on asymmetric hydrogenation of olefins is vital for the synthesis of pharmaceutical molecules and chemical industry. A cobalt-catalyzed enantioconvergent hydrogenation method has been developed for common minimally functionalized E/Z-olefin mixtures.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Yiding Wang, Lei Shen, Helin Wang, Yixin Luo, Qingle Zeng
Summary: The ring-opening addition reaction of activated vinyl cyclopropanes with N-tosylhydrazones in the presence of palladium(0) and triphenylphosphine yields N-tosylhydrazone butenylmalonate compounds. Aromatic aldehyde-derived N-tosylhydrazones produce both terminal and internal N-allylated products, with the terminal products being the major ones. On the other hand, ketone-derived tosylhydrazones only yield terminal addition products. The transformation relationship between the terminal and internal N-allylated products is also observed. A reasonable mechanism based on preliminary experimental results is proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
