Radicals in Action: A Festival of Radical Transformations

Zard, Samir Z.

doi:10.1021/acs.joc.7b00431

Cited by 2 publications

(3 citation statements)

References 10 publications

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“…59−62 Early investigations by Barton, Giese, Curran, and others showed that the addition of carbon-centered radicals to alkenes had significant potential for chemical synthesis outside the polymer arena. 53,63 Trends in reactivity and selectivity of carbon-radical alkene couplings can be described using frontier orbital theory: for nucleophilic radicals, the dominant interactions are those between radical SOMOs and alkene LUMOs and for electrophilic radicals those between radical SOMOs and alkene HOMOs. 64 The total syntheses discussed in this section will be organized by the extent of carbon substitution of the carbon radical.…”

Section: [3+2]mentioning

confidence: 99%

Strategic Use of Visible-Light Photoredox Catalysis in Natural Product Synthesis

2021

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Recent progress in the development of photocatalytic reactions promoted by visible light is leading to a renaissance in the use of photochemistry in the construction of structurally elaborate organic molecules. Because of the rich functionality found in natural products, studies in natural product total synthesis provide useful insights into functional group compatibility of these new photocatalytic methods as well as their impact on synthetic strategy. In this review, we examine total syntheses published through the end of 2020 that employ a visible-light photoredox catalytic step. To assist someone interested in employing the photocatalytic steps discussed, the review is organized largely by the nature of the bond formed in the photocatalytic step.

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Section: [3+2]mentioning

confidence: 99%

Strategic Use of Visible-Light Photoredox Catalysis in Natural Product Synthesis

2021

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“…Pale yellow oil. 1 4-Cyano-2,2-difluoro-6-phenylhexanoate (10). Dry potassium acetate (99 mg, 1 mmol), copper cyanide (49 mg, 0.55 mmol), and DMSO (2 mL) were placed in a screw cap culture tube under argon atmosphere.…”

Section: Synthesis Of Compound 6i (Starting From 2 Mmol Of 1a)mentioning

confidence: 99%

“…2,6−8 Indeed, radicals offer a unique chemoselectivity pattern and wide functional group tolerance. 9,10 The advent of photocatalysis 11−13 has significantly broadened methods for the generation of radicals, which further spurred the development of difunctionalization reactions. 14−17 A strategy of dual photoredox/transition metal catalysis, in which different catalytic systems promote different steps, has gained increasing attention.…”

mentioning

confidence: 99%

Dual Photoredox/Copper Catalyzed Fluoroalkylative Alkene Difunctionalization

2023

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A method for performing radical difunctionalization of alkenes using fluorinated halides and a nucleophilic component (thiolate and iodide anions) is described. These nucleophilic fragments serve as redox active groups for performing subsequent transformations. The difunctionalization reaction involves photoredox generation of fluorinated radicals, their addition to the double bond followed by copperpromoted C−S or C−I bond formation. The primary products can be further coupled with silyl enol ethers, α-(trifluoromethyl)styrenes, and trimethylsilyl cyanide affording a variety of fluorinated compounds.

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Radicals in Action: A Festival of Radical Transformations

Cited by 2 publications

References 10 publications

Strategic Use of Visible-Light Photoredox Catalysis in Natural Product Synthesis

Strategic Use of Visible-Light Photoredox Catalysis in Natural Product Synthesis

Dual Photoredox/Copper Catalyzed Fluoroalkylative Alkene Difunctionalization

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