Silver(I) Promoted the C4–H Bond Phosphonation of 1-Naphthylamine Derivatives with H-Phosphonates

Zhao, Lihua; Sun, Mingming; Yang, Fan; Wu, Yangjie

doi:10.1021/acs.joc.1c00971

Cited by 6 publications

(2 citation statements)

References 53 publications

(21 reference statements)

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“…In recent years, our group has mainly focused on the C–H functionalization of 8-aminoquinoline 10 and 1-naphthylamide derivatives. 11,12 Inspired by the abovementioned previous reports and our own work, we would like to report an easy and efficient protocol for direct cyanoalkoxylation of 1-naphthylamine derivatives with AIBN, thereby establishing a facile and convenient route to 4-cyanoalkoxylation of 1-naphthylamine derivatives (Scheme 1c).…”

Section: Introductionmentioning

confidence: 97%

Ru(iii)-catalyzed C4–H bond cyanoalkoxylation of 1-naphthylamine derivatives with azobisisobutyronitrile

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Section: Introductionmentioning

confidence: 97%

Ru(iii)-catalyzed C4–H bond cyanoalkoxylation of 1-naphthylamine derivatives with azobisisobutyronitrile

et al. 2022

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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

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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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Quinquevalent phosphorus acids

Bałczewski,

Owsianik

2024

Organophosphorus Chemistry

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This chapter shows, as in previous years, the most important achievements of the 2021 year in the area of organo-phosphorus compounds containing: three P–O bonds (Section 2: phosphoric acids and their derivatives), two P–O and one P–C bonds (Section 3: phosphonic acids and their derivatives) as well as one P–O and two P–C bonds (Section 4: phosphinic acids and their derivatives), in addition to the phosphoryl group P═O, present in all three groups of compounds. Each of the main sections covers “synthesis and reactions” including pure synthesis without applications, “synthesis and biological applications” and “synthesis and miscellaneous applications” including synthesis directed towards non-biological applications. At the end of each subsection, the corresponding achievements are shown for hetero-analogues in which phosphorus–oxygen bonds have been replaced by phosphorus–heteroatom P–X and/or P═Y bonds (X, Y = N, S or Se). The subsection on quinquevalent phosphorus acids and their derivatives as catalysts has been placed, as usual, at the end of the entire chapter, after a review of all three main groups of compounds. As in previous years, the area devoted to phosphoric and phosphonic acids and their derivatives dominated over a smaller section of phosphinic acids and their derivatives, and literature references for these sections remained at a ratio of 4 : 12 : 1. A dynamic, five-fold increase in the number of works, in the subject of chiral phosphoric acids as catalysts, has been recorded in this year.

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Silver(I) Promoted the C4–H Bond Phosphonation of 1-Naphthylamine Derivatives with H-Phosphonates

Cited by 6 publications

References 53 publications

Ru(iii)-catalyzed C4–H bond cyanoalkoxylation of 1-naphthylamine derivatives with azobisisobutyronitrile

Ru(iii)-catalyzed C4–H bond cyanoalkoxylation of 1-naphthylamine derivatives with azobisisobutyronitrile

Recent advances in electrochemical C—H phosphorylation

Quinquevalent phosphorus acids

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