PPh<sub>3</sub>/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls

Wadekar, Ketan; Aswale, Suraj; Yatham, Veera Reddy

doi:10.1039/d0ra03211e

Cited by 36 publications

(17 citation statements)

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“…151 More recently, a PPh 3 /NaI-mediated photo-induced alkylarylation radical cascade of 2-isocyanobiaryls toward the synthesis of phenanthridines was documented. 152 The Taylor and Donald and group developed a novel method for the reductive generation of carbamoyl radicals A from the corresponding NHPI oxamide derivatives 188 under Ir-catalyzed visible photoredox catalysis (Scheme 82). 153 The resulting carbamoyl radical underwent tandem annulation with electron-deficient alkenes 189 through an intermolecular addition and cyclization process, affording a diverse collection of highly important 154 Importantly, the reaction was found to be compatible with a range of alkenoic acids and NHPI esters derived from primary, secondary, and tertiary carboxylic acids.…”

Section: •+mentioning

confidence: 99%

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

et al. 2021

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The past decade has witnessed the emergence of N-(acyloxy)phthalimides (NHPI esters) and its derivatives at the forefront of synthetic methods facilitating the construction of diverse molecular frameworks from the readily available carboxylic acid feedstock. The NHPI esters are predisposed to undergo reductive fragmentation via a single electron transfer (SET) process under thermal, photochemical, or electrochemical conditions to generate the corresponding carbon-or nitrogencentered radicals that participate in a multitude of synthetic transformations to forge carbon−carbon and carbon−heteroatom bonds. The chemistry involving NHPI esters has received broad applicability not only in well-designed cascade annulations but also in medicinal chemistry and natural product synthesis. This comprehensive Review, broadly categorized according to the nature of the bond formation, details the progress made in this field since the initial discovery by providing representative examples with mechanistic details, with an emphasis on challenges and future directions.

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Section: •+mentioning

confidence: 99%

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

et al. 2021

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“…Yatham et al. disclosed a simple metal‐free synthetic route to construct 6‐substituted phenanthridines 331 through photocatalytic decarboxylative cascade cyclization of 2‐isocyanobiaryls 210 with alkyl N ‐hydroxyphthalimide (NHP) esters 330 using a cheap PPh 3 /NaI system as the photocatalyst [97] . After series of optimization studies, using 20 mol% PPh 3 with 100 mol% of sodium iodide in CH 3 CN solvent under irradiation of blue LEDs at 80 °C for 1 h was found to furnish the maximum yield for the reaction.…”

Section: Synthesis Of Phenanthridinesmentioning

confidence: 99%

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

et al. 2021

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Phenanthridine derivatives are one of the most intensively studied families of biologically active compounds. There has been considerable scientific interest in the turn of this century in the synthesis of these N‐containing heterocycles as they are prevalent in many alkaloids and also possess striking biological activities including antibacterial, antifungal, antitumor activities. In this regard, a number of synthetic approaches toward the construction of phenanthridine moieties with various substituents, and to increase their yield have been developed by the synthetic organic community. Even though many researchers have developed various innovative methods for the synthesis of phenanthridine derivatives for the past few years, still there is substantial scope for the discovery of novel synthetic methods. In this review, the latest developments in the diverse synthetic strategies of phenanthridine derivatives in the presence and absence of metals were described. The present review also enlightens the use of different reagents, the diversity of the substrates identified, and the plausible mechanisms unravelled towards the construction of these biologically relevant scaffolds.

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“…[10] The iodidebased activation was found to be quite versatile and was used for various synthetic transformations. [11] At the same time, iodine atom can act as an acceptor (A) in a given EDA complex if it is bound to electron withdrawing fluoroalkyl group. The interaction is well known as halogen bonding [12] and was utilized for the development of catalystfree visible light induced radical fluoroalkylation reactions.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light‐Promoted Reversible Sulfide/Iodide Exchange in Fluoroalkyl Sulfides Enabled by Electron Donor‐Acceptor Complex Formation

2021

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Catalyst-free visible-light-mediated exchange of two photoredox active groups, a 4-perfluoropyridinylthio group and an iodide group, attached to a fluorinated alkyl fragment is described. The reaction can be preparatively performed in both directions by appropriate choice of wavelength, solvent, and counterion. In the forward reaction, alkyl sulfide interacts with an iodide anion to give alkyl iodide and a thiolate anion, with the driving force provided by blue light (455 nm). In the backward process, fluorinated alkyl iodide interacts with the thiolate under violet light (400 nm). The reactions proceed through the formation of electron donor-acceptor (EDA) complexes, which were observed by UV/Vis absorption or NMR spectroscopies. Evidence of the sulfur-iodide interaction was supported by X-ray analysis.

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PPh₃/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls

Abstract: PPh3/NaI driven photocatalytic decarboxylative cyclization of 2-isocyanobiaryls with alkyl NHP esters was developed. This simple protocol afforded a novel and environmentally friendly approach to furnish 6-alkyl phenanthridines in good yields.

Cited by 36 publications

References 61 publications

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

Visible‐Light‐Promoted Reversible Sulfide/Iodide Exchange in Fluoroalkyl Sulfides Enabled by Electron Donor‐Acceptor Complex Formation

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PPh3/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls

Abstract: PPh3/NaI driven photocatalytic decarboxylative cyclization of 2-isocyanobiaryls with alkyl NHP esters was developed. This simple protocol afforded a novel and environmentally friendly approach to furnish 6-alkyl phenanthridines in good yields.

Cited by 36 publications

References 61 publications

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Single Electron Transfer-Induced Redox Processes Involving N-(Acyloxy)phthalimides

Recent Trends in the Synthesis and Mechanistic Implications of Phenanthridines

Visible‐Light‐Promoted Reversible Sulfide/Iodide Exchange in Fluoroalkyl Sulfides Enabled by Electron Donor‐Acceptor Complex Formation

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PPh₃/NaI driven photocatalytic decarboxylative radical cascade alkylarylation reaction of 2-isocyanobiaryls