Effects of Alkoxy Groups on Arene Rings of Lignin β-O-4 Model Compounds on the Efficiencies of Single Electron Transfer-Promoted Photochemical and Enzymatic C–C Bond Cleavage Reactions

Suk Hyun Lim; Keepyung Nahm; Choon Sup Ra; Dae Won Cho; Ung Chan Yoon; John A. Latham; Debra Dunaway-Mariano; Patrick S. Mariano

doi:10.1021/jo401680z

Effects of Alkoxy Groups on Arene Rings of Lignin β-O-4 Model Compounds on the Efficiencies of Single Electron Transfer-Promoted Photochemical and Enzymatic C–C Bond Cleavage Reactions

The Journal of Organic Chemistry ◽

10.1021/jo401680z ◽

2013 ◽

Vol 78 (18) ◽

pp. 9431-9443 ◽

Cited By ~ 29

Author(s):

Suk Hyun Lim ◽

Keepyung Nahm ◽

Choon Sup Ra ◽

Dae Won Cho ◽

Ung Chan Yoon ◽

...

Keyword(s):

Electron Transfer ◽

Bond Cleavage ◽

Single Electron ◽

Single Electron Transfer ◽

Model Compounds ◽

Cleavage Reactions ◽

Alkoxy Groups

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Single electron transfer rate measurements interpretation when a radicalion bond cleavage reaction occurs within the encounter pair

Journal of Electroanalytical Chemistry ◽

10.1016/0022-0728(86)90221-4 ◽

1986 ◽

Vol 205 (1-2) ◽

pp. 35-42 ◽

Cited By ~ 5

Author(s):

James Grimshaw ◽

Norris Thompson

Keyword(s):

Electron Transfer ◽

Transfer Rate ◽

Bond Cleavage ◽

Single Electron ◽

Single Electron Transfer ◽

Electron Transfer Rate ◽

Cleavage Reaction ◽

Bond Cleavage Reaction

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Reactions of Metal Ion Complexes with Lignin Model Compounds Part I. Co(TSPP) as a Single Electron Transfer Catalyst and Implications for the Mechanism of AQ Pulping

Journal of Wood Chemistry and Technology ◽

10.1080/02773819308020523 ◽

1993 ◽

Vol 13 (3) ◽

pp. 371-389 ◽

Cited By ~ 10

Author(s):

Paul A. Watson ◽

L. James Wright ◽

Terry J. Fullerton

Keyword(s):

Electron Transfer ◽

Metal Ion ◽

Single Electron ◽

Single Electron Transfer ◽

Model Compounds ◽

Metal Ion Complexes ◽

Lignin Model Compounds ◽

Lignin Model

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Single Electron Transfer-Mediated Selectiveendo- andexocyclic Bond Cleavage Processes in Azaphosphiridine Chromium(0) Complexes: A Computational Study

Inorganic Chemistry ◽

10.1021/ic300522g ◽

2012 ◽

Vol 51 (13) ◽

pp. 7250-7256 ◽

Cited By ~ 18

Author(s):

Arturo Espinosa ◽

Celia Gómez ◽

Rainer Streubel

Keyword(s):

Electron Transfer ◽

Computational Study ◽

Bond Cleavage ◽

Single Electron ◽

Single Electron Transfer

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Photodegradation of Oligomeric Polyesters Containing Anthraquinone and 1,2-Diamine Units. Single Electron Transfer Induced Cation Radical Bond Cleavage in the Solid State

Journal of the American Chemical Society ◽

10.1021/ja00113a012 ◽

1995 ◽

Vol 117 (8) ◽

pp. 2226-2235 ◽

Cited By ~ 4

Author(s):

Jeffrey W. Leon ◽

David G. Whitten

Keyword(s):

Electron Transfer ◽

Solid State ◽

Bond Cleavage ◽

Cation Radical ◽

Single Electron ◽

Single Electron Transfer

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Organic chemistry of subvalent transition metal complexes. 12. Hydrodesulfurization of organosulfur heterocycles by metal hydride-nickel(0) complexes: accelerated single-electron transfer in carbon-sulfur bond cleavage

Journal of the American Chemical Society ◽

10.1021/ja00284a045 ◽

1986 ◽

Vol 108 (24) ◽

pp. 7763-7767 ◽

Cited By ~ 49

Author(s):

john J. Eisch ◽

Lawrence E. Hallenbeck ◽

Kyoung Im. Han

Keyword(s):

Organic Chemistry ◽

Electron Transfer ◽

Transition Metal ◽

Metal Complexes ◽

Transition Metal Complexes ◽

Metal Hydride ◽

Bond Cleavage ◽

Single Electron ◽

Single Electron Transfer ◽

Sulfur Bond

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ChemInform Abstract: Organic Chemistry of Subvalent Transition Metal Complexes. Part 12. Hydrodesulfurization of Organosulfur Heterocycles by Metal Hydride-Nickel(0) Complexes: Accelerated Single-Electron Transfer in Carbon-Sulfur Bond Cleavage.

ChemInform ◽

10.1002/chin.198716143 ◽

1987 ◽

Vol 18 (16) ◽

Author(s):

J. J. EISCH ◽

L. E. HALLENBECK ◽

K. I. HAN

Keyword(s):

Organic Chemistry ◽

Electron Transfer ◽

Transition Metal ◽

Metal Complexes ◽

Transition Metal Complexes ◽

Metal Hydride ◽

Bond Cleavage ◽

Single Electron ◽

Single Electron Transfer ◽

Sulfur Bond

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Visible-Light-Mediated Photocatalytic Oxidative C–C Bond Cleavage of Geminal Diazides: An Approach to Oxamates

SynOpen ◽

10.1055/s-0040-1706048 ◽

2021 ◽

Vol 05 (02) ◽

pp. 152-157

Author(s):

Duddu S. Sharada ◽

Narenderreddy Katta ◽

Arumugavel Murugan ◽

Sonika Sharma

Keyword(s):

Electron Transfer ◽

Visible Light ◽

Bond Cleavage ◽

Organic Dye ◽

Single Electron ◽

Mechanistic Study ◽

Single Electron Transfer ◽

Photoredox Catalysis ◽

The Past ◽

Remarkable Progress

AbstractPhotoredox catalysis has received great attention in both academia and industry and remarkable progress has been made over the past decade. Now, it has been shown that a visible-light-mediated oxidative C–C bond cleavage of geminal diazides can be induced by organic dye catalysis for the synthesis of oxamates. A mechanistic study, confirmed by control experiments, indicates that this proceeds through single-electron transfer (SET). This methodology can be applied to convert a wide array of geminal diazides into oxamates.

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Regioselectivity of Enzymatic and Photochemical Single Electron Transfer Promoted Carbon−Carbon Bond Fragmentation Reactions of Tetrameric Lignin Model Compounds

The Journal of Organic Chemistry ◽

10.1021/jo200253v ◽

2011 ◽

Vol 76 (8) ◽

pp. 2840-2852 ◽

Cited By ~ 24

Author(s):

Dae Won Cho ◽

John A. Latham ◽

Hea Jung Park ◽

Ung Chan Yoon ◽

Paul Langan ◽

...

Keyword(s):

Electron Transfer ◽

Single Electron ◽

Single Electron Transfer ◽

Model Compounds ◽

Lignin Model Compounds ◽

Carbon Bond ◽

Carbon Carbon Bond ◽

Lignin Model ◽

Fragmentation Reactions

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Cryovoltammetrically probing functional group reductive cleavage: alkyl–sulfur versus aryl–sulfur bond cleavage in an alkyl naphthyl thioether under single electron-transfer is temperature switchable

Chemical Communications ◽

10.1039/b606638k ◽

2006 ◽

pp. 3402-3404 ◽

Cited By ~ 11

Author(s):

Christopher A. Paddon ◽

Farrah L. Bhatti ◽

Timothy J. Donohoe ◽

Richard G. Compton

Keyword(s):

Electron Transfer ◽

Functional Group ◽

Bond Cleavage ◽

Reductive Cleavage ◽

Single Electron ◽

Single Electron Transfer ◽

Sulfur Bond

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Photoinduced transition-metal and external photosensitizer free cross-coupling of aryl triflates with trialkyl phosphites

Chemical Communications ◽

10.1039/d1cc03496k ◽

2021 ◽

Author(s):

Qian Dou ◽

Li Geng ◽

Bin Cheng ◽

Chao-Jun Li ◽

Huiying Zeng

Keyword(s):

Electron Transfer ◽

Transition Metal ◽

Bond Cleavage ◽

Cross Coupling ◽

Single Electron ◽

Single Electron Transfer ◽

Rearrangement Process ◽

Trialkyl Phosphites

Photoinduced phosphonation of aryl triflates with trialkyl phosphites via a tandem single-electron-transfer, C–O bond cleavage and Arbuzov rearrangement process in the absence of transition-metal and external photosensitizer is reported herein....

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