Recent advances of visible-light photocatalysis in the functionalization of organic compounds

Journal of Photochemistry and Photobiology C Photochemistry Reviews, Journal Year: 2022, Volume and Issue: 50, P. 100488 - 100488

Published: Feb. 2, 2022

Language: Английский

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Photophysical Properties and Redox Potentials of Photosensitizers for Organic Photoredox Transformations

Synlett, Journal Year: 2021, Volume and Issue: 33(12), P. 1154 - 1179

Published: Feb. 15, 2021

Abstract Photoredox catalysis has proven to be a powerful tool in synthetic organic chemistry. The rational design of photosensitizers with improved photocatalytic performance constitutes major advancement photoredox transformations. This review summarizes the fundamental ground-state and excited-state photophysical electrochemical attributes molecular photosensitizers, which are important determinants their reactivity.

Language: Английский

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Metallaphotoredox-enabled aminocarboxylation of alkenes with CO2

Nature Catalysis, Journal Year: 2023, Volume and Issue: 6(10), P. 959 - 968

Published: Sept. 21, 2023

Language: Английский

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Enantioselective Cyanofunctionalization of Aromatic Alkenes via Radical Anions

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(2), P. 1410 - 1422

Published: Jan. 5, 2024

Alkene radical ions constitute an integral and unique class of reactive intermediates for the synthesis valuable compounds because they have both unpaired spins charge. However, relatively few synthetic applications alkene anions emerged due to a dearth generally applicable mild anion generation approaches. Precise control over chemo- stereoselectivity in anion-mediated processes represents another long-standing challenge their high reactivity. To overcome these issues, here, we develop new redox-neutral strategy that seamlessly merges photoredox copper catalysis enable controlled orthogonal enantioselective cyanofunctionalization via distonic-like species. This enables highly regio-, chemo-, hydrocyanation, deuterocyanation, cyanocarboxylation alkenes without stoichiometric reductants or oxidants under visible light irradiation. protocol provides blueprint exploration transformation potential anions.

Language: Английский

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Reductive Activation and Hydrofunctionalization of Olefins by Multiphoton Tandem Photoredox Catalysis

ACS Catalysis, Journal Year: 2021, Volume and Issue: 11(9), P. 5472 - 5480

Published: April 20, 2021

The conversion of olefin feedstocks to architecturally complex alkanes represents an important strategy in the expedient generation valuable molecules for chemical and life sciences. Synthetic approaches are reliant on electrophilic activation unactivated olefins, necessitating functionalization with nucleophiles. However, reductive less activated olefins electrophiles remains ongoing challenge synthetic chemistry. Here, we report nucleophilic inert styrenes through a photoinduced direct single electron reduction corresponding radical anion. Central this approach is multiphoton tandem photoredox cycle iridium photocatalyst [Ir(ppy)2(dtb-bpy)]PF6, which triggers situ formation high-energy photoreductant that selectively reduces styrene olefinic π bonds anions without stoichiometric reductants or dissolving metals. This mild enables chemoselective hydrofunctionalization furnish alkane tertiary alcohol derivatives. Mechanistic studies support anion intermediate Birch-type involving two sequential transfers. Overall, complementary mode achieves alkenes electrophiles, adding value abundant as building blocks modern protocols.

Language: Английский

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Redox-neutral carbon–heteroatom bond formation under photoredox catalysis

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(46), P. 7004 - 7027

Published: Jan. 1, 2023

This feature article presents all the recent reports on photoredox-catalyzed redox-neutral carbon–heteroatom coupling reactions up to March 2023.

Language: Английский

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Reductive Cleavage of C–X or N–S Bonds Catalyzed by Super Organoreductant CBZ6

Organic Letters, Journal Year: 2023, Volume and Issue: 25(5), P. 816 - 820

Published: Jan. 24, 2023

The reductive cleavage of C(Ar)-X bonds is the key step for cross coupling Ar-X with other groups. In this work, under irradiation 407 nm LEDs using sodium formate as reductant and thiol hydrogen atom transfer agent, a variety (hetero)aryl chlorides, bromides, iodides could be reduced to corresponding (hetero)arenes. intermediates, aryl radicals, trapped by either hydrogen, phosphite, or borates. same reduction conditions can extended deprotection sulfonamides.

Language: Английский

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Photocatalytic low-temperature defluorination of PFASs

Nature, Journal Year: 2024, Volume and Issue: 635(8039), P. 610 - 617

Published: Nov. 20, 2024

Language: Английский

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Photocatalytic Reductive Functionalization of Aryl Alkynes via Alkyne Radical Anions

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9283 - 9293

Published: June 4, 2024

The direct reductive functionalization of alkynes under mild conditions presents a promising yet challenging avenue for accessing value-added molecules. Alkyne radical anions represent distinct class reactive intermediates characterized by both charge and an unpaired electron, thus holding great potential facilitating diverse bond formations, particularly in alkyne functionalization. However, the synthetic utility is limited, primarily due to difficulty their generation formation highly unstable vinyl intermediates. In this study, we accomplished from aryl feedstocks via single electron transfer (SET) reduction with photogenerated CO2 anion (CO2•–), enabling hydroalkylation, arylalkenylation, hydrocarboxylation alkynes. Our photocatalytic strategy features metal-free catalysis, reaction conditions, employment traceless reductant, good functional group compatibility, step- atom-economy, high regioselectivity. This study not only paves way leveraging underexplored but also catalyzes ongoing exploration bifunctional CO2•– species chemistry.

Language: Английский

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Photoinduced Desaturation of Amides by Palladium Catalysis

Organic Letters, Journal Year: 2022, Volume and Issue: 24(35), P. 6460 - 6465

Published: Aug. 30, 2022

A photoinduced palladium-catalyzed desaturation method that is suitable for converting the linear amides to their α,β-unsaturated counterparts reported. The reaction does not require strong base/acid or sulfur/selenium and oxidant reagents can be carried out at room temperature through a simple one-step operation. protocol exhibits great scalability functional group tolerance. mechanism has been investigated deuterium labeling experiments, radical clock, capture, kinetic studies. Mechanistic studies suggested pathway involving aryl/alkyl Pd-radical intermediates.

Language: Английский

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