Electrochemical rearrangement protocols towards the construction of diverse molecular frameworks

Saha, Debarshi; Taily, Irshad Maajid; Kumar, Rakesh; Banerjee, Prabal

doi:10.1039/d1cc00116g

Cited by 22 publications

(13 citation statements)

References 87 publications

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“…Liang S. et al 47 reviewed the anodic construction of heterocycles via the electrochemical method from 2018 to 2019. In 2021, Saha et al 48 reviewed the synthesis of complex molecular frameworks through electrochemically mediated rearrangement reactions. In the same year, Z. Meng et al 49 outlined reports on the formation of the C–N bond via the electrochemical method since 2015.…”

Section: Introductionmentioning

confidence: 99%

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

et al. 2022

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Section: Introductionmentioning

confidence: 99%

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

et al. 2022

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“…14−16 Electrochemical synthesis has been widely used in C−H bond functionalization, 17 C−C 18 and C−N 19 bond formation, and diverse electrochemical rearrangement protocols. 20 Very recently, Li's group reported the electrochemical generation of a stabilized azomethine ylide followed by cycloaddition toward the synthesis of polycyclic N-heterocycles. 21 Followed by this work, Masson et al documented an electrochemical tandem radical trifluoromethylation of allylamines via 1,3-dipolar cycloaddition toward the construction of CF 3 containing imidazolines and oxazolidines.…”

Section: ■ Introductionmentioning

confidence: 87%

“…The history of electrochemical synthesis began in the 20th century, where Shono and Yoshida worked extensively in electroorganic oxidation of unfunctionalized amides via an N -acyliminium ion . Later, the 21st century brings renaissance in the field of electrochemical synthesis due to its prime advantages of superior environment and economic acceptance over the traditional chemical and photochemical processes. − Electrochemical synthesis has been widely used in C–H bond functionalization, C–C and C–N bond formation, and diverse electrochemical rearrangement protocols . Very recently, Li’s group reported the electrochemical generation of a stabilized azomethine ylide followed by cycloaddition toward the synthesis of polycyclic N -heterocycles .…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles

Kumar

Banerjee

2021

J. Org. Chem.

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Azomethine ylides are fascinating 1,3-dipoles for [3 + 2] cycloaddition reactions toward the construction of N-heterocycles. Herein, an efficient and environmentally benign electrochemical approach for the generation of a nonstabilized azomethine ylide has been established under metal-free and external oxidant-free conditions. The resulting 1,3-dipole undergoes a [3 + 2] cycloaddition reaction with olefins. This electrosynthetic methodology indulges a straightforward and facile approach for the construction of substituted pyrrolidines.

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“…In the previous decade, electroorganic synthesis has come up as an invincible tool for carrying out several valuable organic transformations [17] . Engaging the traceless electrons, a variety of anodic processes such as decarboxylation, [18] alkene bifunctionalization, [19] rearrangements, [20] annulations, [21] C‐heteroatom bond formation [22] has been disclosed. Recently, our group has also documented a protocol for the in‐situ generation of isocyanates [23] .…”

Section: Methodsmentioning

confidence: 99%

Electricity Driven 1,3‐Oxohydroxylation of Donor‐Acceptor Cyclopropanes: a Mild and Straightforward Access to β‐Hydroxy Ketones

2021

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An unprecedented external oxidant-free electrochemical protocol for 1, 3-oxohydroxylation of donor-acceptor cyclopropane is disclosed. The strategy encompasses the activation of the labile π-electron cloud of the aryl ring to cleave the strained C sp 3 À C sp 3 bond of cyclopropane to afford the β-hydroxy ketones via insertion of molecular oxygen. More significantly, based on the detailed mechanistic investigations and cyclic voltammetry experiments, a plausible mechanism is proposed.The magnificent journey of the most strained carbocycle named cyclopropane began long back in the 1970s. [1] The fundamentals laid by the frontiers have enabled the scientific community to exploit them for the construction of several complex molecular architectures cleverly. Bearing the ring strain of 115 KJ mol À 1 with an inefficient orbital overlap induces a significant amount of π-character in the bent CÀ C bonds of Cylclopropanes. [2] Further, the introduction of the donor and acceptor groups at the vicinal position of these CÀ C bonds induces a push-pull effect which polarizes the cycloalkane. [3] The previous decade has encountered a huge renaissance in the area of donor-acceptor cyclopropanes (DACs). [4] However, most of these documented protocols rely on the concept of Lewis [5] or Bronsted acid [6] catalysis, which cleaves the CÀ C bond in a heterolytic fashion and renders a zwitterionic species. [4] These 1,3-dipole species have been utilized for several cycloadditions, [7] rearrangements, [8] and ring-opening reactions. [9] Among them, 1,3-bifunctionalization of these DACs are still rare and relatively underexplored. However, there are several reports which demonstrate that these 1,3-dipoles can be seized with amines, [10a] azides, [10b] phenols, [10c] thiols [10d] etc. wherein, the ensuing anion traps the proton. In 2011, Sparr and Gilmour manifested the enantioselective 1,3-dichlorination of cyclopropane carbaldehyde in an organocatalytic fashion. [11] Later, in 2014, Werz and coworkers disclosed the ring-opening 1,3-dichlorination in the presence of iodobenzene dichloride (Scheme 1a). [12a] Followed by this, in 2017, the same group documented the reactivity of DACs with chalcogenyl chloride and bromides (Scheme 1b). [12b-c] In continuation to the endeav-[a

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Electrochemical rearrangement protocols towards the construction of diverse molecular frameworks

Abstract: Rearrangement reactions constitute a critical facet of synthetic organic chemistry and demonstrate an attractive way to take advantage of existing structures to access various important molecular frameworks. Electroorganic chemistry has...

Cited by 22 publications

References 87 publications

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Electrochemical Generation of a Nonstabilized Azomethine Ylide: Access to Substituted N-Heterocycles

Electricity Driven 1,3‐Oxohydroxylation of Donor‐Acceptor Cyclopropanes: a Mild and Straightforward Access to β‐Hydroxy Ketones

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