Ag(I)-catalyzed synthesis of (E)-alkenyl phosphonates by oxidative coupling of H-phosphites with β-nitroolefins

Ma, Li; Shang, Shengjie; Yuan, Hua; Zhang, Yue; Zeng, Zhigang; Chen, Yunfeng

doi:10.1016/j.tetlet.2021.153530

Cited by 7 publications

(3 citation statements)

References 71 publications

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“…受屈凌波课题组的启发, 陈云峰课题组 [67] 在 2021 年发现亚磷酸酯与 β-烷基硝基苯乙烯在硝酸银催化下, 以乙腈为溶剂, Ni(NO 3 ) 2 •6H 2 O 为氧化剂时, 可以很大程度上抑制 β-硝基烯烃不必要的异构化反应, 选择性地生成(E)-烯基膦酸酯, 收率高达 83% (Eq. 31).…”

Section: 类似地屈凌波课题组unclassified

Research Progress on Reactions Involving β-Nitrostyrene

Li,

Sun,

Zhao

et al. 2023

Chinese Journal of Organic Chemistry

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β-Nitrostyrene has a variety of biological activities and is also an important intermediate in organic synthesis, which can participate in a variety of chemical reactions due to its active chemical properties, and has attracted extensive attention from researchers. The reactions involving nitrostyrene compounds in recent years are summarized, and the reaction are divided into denitrification reactions and carbon-carbon double bonds according to reaction sites, expecting to provide a reference for new reactions with β-nitrostyrene compounds as substrates. Keywords β-nitrostyrene; denitrogenation reaction; carbon carbon double bond reaction β-硝基苯乙烯是重要的有机化合物, 广泛存在于具有多种生物活性的化合物结构和药物分子中, 其本身也具有抑制人端粒酶 [1] 、杀菌 [2][3] 及抗肿瘤 [4][5] 等活性. 近年来, 其在有机合成方向的应用也越来越被重视.

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Section: 类似地屈凌波课题组unclassified

Research Progress on Reactions Involving β-Nitrostyrene

Li,

Sun,

Zhao

et al. 2023

Chinese Journal of Organic Chemistry

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“…[ 10 ] Recently, Chen, Zeng and co‐workers demonstrated a highly selective synthesis of aryl, alkyl substituted vinylphosphonates via the addition of phosphoryl radical to β ‐nitroolefins, and the marked electronic and spatial difference between aryl and alky groups laid the foundation for this success (Figure 1). [ 11 ] Obviously, the stereochemical control with two different aryl groups is more challenging, and only limited examples with poor stereoselectivity were scattered in the literatures. [ 10a,b,d ] Liu, Dai, and co‐workers reported the palladium‐catalyzed cross‐ coupling of β‐diazophosphonates with arylhalides, and only the substrate with phenyl and thienyl substitutions offered moderate stereoselectivity ( E / Z = 5.5: 1) (Figure 1b).…”

Section: Background and Originality Contentmentioning

confidence: 99%

Highly Stereoselective Synthesis of 2,2‐Disubstituted Vinylphosphonates via Aryl to Vinyl 1,4‐Palladium Migration

et al. 2022

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Vinylphosphates play an important role in the fields of synthetic chemistry, pharmaceuticals and material science. It is a long-standing challenge to control the geometry of multi-substituted vinylphosphates. Herein, an efficient method for the synthesis of 2,2-disubstituted vinylphosphonates has been reported. The reaction proceeded via aryl to vinyl 1,4-palladium migration progress, in which two difficulties that the deactivation of palladium catalyst by the coordination of excess secondary phosphine oxide and the competitive cross-coupling to form arylphosphonates are successfully overcome. The judicious selection of phosphine ligand is the key to success. This protocol features excellent regio-and stereoselectivitiy, generally excellent reaction yields and broad substrate socpe.

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“…( Hirao et al, 1981 ; Petrakis and Nagabhushan, 1987 ; Gelman et al, 2003 ; Vaillard et al, 2007 ; Andaloussi et al, 2009 ; Luo and Wu, 2009 ; Berrino et al, 2010 ; Bruch et al, 2010 ; Zhuang et al, 2011 ; Zhao et al, 2012 ; Hu et al, 2013 ). Recently, new variants of C–H bond phosphorylation have been proposed, for example, transition metal catalysis ( Klein et al, 2007 ; Budnikova and Sinyashin, 2015 ; Budnikova et al, 2017 ; Shen et al, 2019 ; Liu et al, 2021b ; Guo et al, 2021 ; Ma et al, 2021 ; Zhao et al, 2021 ; Li et al, 2022a ; Li et al, 2022b ; Chen et al, 2022 ; Ji et al, 2022 ) or radical aromatic phosphorylation ( Gao et al, 2017 ; Gao et al, 2018 ; Cai et al, 2019 ; Mai et al, 2019 ; Chen et al, 2020 ; Liu et al, 2020 ; Rawat et al, 2020 ) (photoinitiated or catalyzed by the same metals or other activators), which provide a direct atom-economical road to C-P functionalized products of different nature (alkenes, alkanes, arenes).…”

Section: Introductionmentioning

confidence: 99%

Recent advances in electrochemical C—H phosphorylation

et al. 2022

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The activation of C–H bond, and its direct one-step functionalization, is one of the key synthetic methodologies that provides direct access to a variety of practically significant compounds. Particular attention is focused on modifications obtained at the final stages of the synthesis of complicated molecules, which requires high tolerance to the presence of existing functional groups. Phosphorus is an indispensable element of life, and phosphorus chemistry is now experiencing a renaissance due to new emerging applications in medicinal chemistry, materials chemistry (polymers, flame retardants, organic electronics, and photonics), agricultural chemistry (herbicides, insecticides), catalysis (ligands) and other important areas of science and technology. In this regard, the search for new, more selective, low-waste synthetic routes become relevant. In this context, electrosynthesis has proven to be an eco-efficient and convenient approach in many respects, where the reagents are replaced by electrodes, where the reactants are replaced by electrodes, and the applied potential the applied potential determines their “oxidizing or reducing ability”. An electrochemical approach to such processes is being developed rapidly and demonstrates some advantages over traditional classical methods of C-H phosphorylation. The main reasons for success are the exclusion of excess reagents from the reaction system: such as oxidants, reducing agents, and sometimes metal and/or other improvers, which challenge isolation, increase the wastes and reduce the yield due to frequent incompatibility with these functional groups. Ideal conditions include electron as a reactant (regulated by applied potential) and the by-products as hydrogen or hydrocarbon. The review summarizes and analyzes the achievements of electrochemical methods for the preparation of various phosphorus derivatives with carbon-phosphorus bonds, and collects data on the redox properties of the most commonly used phosphorus precursors. Electrochemically induced reactions both with and without catalyst metals, where competitive oxidation of precursors leads to either the activation of C-H bond or to the generation of phosphorus-centered radicals (radical cations) or metal high oxidation states will be examined. The review focuses on publications from the past 5 years.

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Ag(I)-catalyzed synthesis of (E)-alkenyl phosphonates by oxidative coupling of H-phosphites with β-nitroolefins

Cited by 7 publications

References 71 publications

Research Progress on Reactions Involving β-Nitrostyrene

Research Progress on Reactions Involving β-Nitrostyrene

Highly Stereoselective Synthesis of 2,2‐Disubstituted Vinylphosphonates via Aryl to Vinyl 1,4‐Palladium Migration

Recent advances in electrochemical C—H phosphorylation

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