A mechanistic investigation of the photoinduced, copper-mediated cross-coupling of an aryl thiol with an aryl halide

A mechanistic study establishes the viability of a copper-mediated pathway for photoinduced C–S cross-coupling involving single electron transfer and in-cage radical recombination.

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Inside Cover: Oxidative Cross-Coupling of Arenes Induced by Single-Electron Transfer Leading to Biaryls by Use of Organoiodine(III) Oxidants (Angew. Chem. Int. Ed. 7/2008)

Angewandte Chemie International Edition ◽

10.1002/anie.200890019 ◽

2008 ◽

Vol 47 (7) ◽

pp. 1154-1154

Author(s):

Toshifumi Dohi ◽

Motoki Ito ◽

Koji Morimoto ◽

Minako Iwata ◽

Yasuyuki Kita

Keyword(s):

Electron Transfer ◽

Cross Coupling ◽

Single Electron ◽

Single Electron Transfer

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Microfluidic electrochemistry for single-electron transfer redox-neutral reactions

Science ◽

10.1126/science.aba3823 ◽

2020 ◽

Vol 368 (6497) ◽

pp. 1352-1357 ◽

Cited By ~ 15

Author(s):

Yiming Mo ◽

Zhaohong Lu ◽

Girish Rughoobur ◽

Prashant Patil ◽

Neil Gershenfeld ◽

...

Keyword(s):

Electron Transfer ◽

Molecular Diffusion ◽

Microfluidic Channel ◽

Cross Coupling ◽

Reactive Intermediates ◽

Single Electron ◽

Visible Light Photocatalysis ◽

Single Electron Transfer ◽

Selective Transformation ◽

Crystal Compound

Electrochemistry offers opportunities to promote single-electron transfer (SET) redox-neutral chemistries similar to those recently discovered using visible-light photocatalysis but without the use of an expensive photocatalyst. Herein, we introduce a microfluidic redox-neutral electrochemistry (μRN-eChem) platform that has broad applicability to SET chemistry, including radical-radical cross-coupling, Minisci-type reactions, and nickel-catalyzed C(sp2)–O cross-coupling. The cathode and anode simultaneously generate the corresponding reactive intermediates, and selective transformation is facilitated by the rapid molecular diffusion across a microfluidic channel that outpaces the decomposition of the intermediates. μRN-eChem was shown to enable a two-step gram-scale electrosynthesis of a nematic liquid crystal compound, demonstrating its practicality.

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Innentitelbild: Oxidative Cross-Coupling of Arenes Induced by Single-Electron Transfer Leading to Biaryls by Use of Organoiodine(III) Oxidants (Angew. Chem. 7/2008)

Angewandte Chemie ◽

10.1002/ange.200890019 ◽

2008 ◽

Vol 120 (7) ◽

pp. 1170-1170

Author(s):

Toshifumi Dohi ◽

Motoki Ito ◽

Koji Morimoto ◽

Minako Iwata ◽

Yasuyuki Kita

Keyword(s):

Electron Transfer ◽

Cross Coupling ◽

Single Electron ◽

Single Electron Transfer

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A Mechanistic Study of the Reactions of Geminal Dihalides with LDA. Evidence for a Single Electron Transfer Pathway in the Reaction of Geminal Diiodides

The Journal of Organic Chemistry ◽

10.1021/jo00108a032 ◽

1995 ◽

Vol 60 (3) ◽

pp. 663-672 ◽

Cited By ~ 8

Author(s):

E. C. Ashby ◽

Abhay K. Deshpande ◽

Girish S. Patil

Keyword(s):

Electron Transfer ◽

Single Electron ◽

Mechanistic Study ◽

Single Electron Transfer ◽

Electron Transfer Pathway

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Oxidative Cross-Coupling of Arenes Induced by Single-Electron Transfer Leading to Biaryls by Use of Organoiodine(III) Oxidants

Angewandte Chemie ◽

10.1002/ange.200704495 ◽

2008 ◽

Vol 120 (7) ◽

pp. 1321-1324 ◽

Cited By ~ 55

Author(s):

Toshifumi Dohi ◽

Motoki Ito ◽

Koji Morimoto ◽

Minako Iwata ◽

Yasuyuki Kita

Keyword(s):

Electron Transfer ◽

Cross Coupling ◽

Single Electron ◽

Single Electron Transfer

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ChemInform Abstract: Transition-Metal-Free Cross-Coupling Reactions by Single Electron Transfer (SET).

ChemInform ◽

10.1002/chin.201442182 ◽

2014 ◽

Vol 45 (42) ◽

pp. no-no

Author(s):

Suresh Kumar Sythana ◽

Santhosh Unni ◽

Yogesh M. Kshirsagar ◽

Pundlik R. Bhagat

Keyword(s):

Electron Transfer ◽

Transition Metal ◽

Cross Coupling ◽

Single Electron ◽

Single Electron Transfer ◽

Coupling Reactions ◽

Metal Free ◽

Cross Coupling Reactions

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Palladium-mediated radical homocoupling reactions: a surface catalytic insight

Catalysis Science & Technology ◽

10.1039/c8cy00901e ◽

2018 ◽

Vol 8 (18) ◽

pp. 4766-4773 ◽

Cited By ~ 6

Author(s):

Isabelle Favier ◽

Marie-Lou Toro ◽

Pierre Lecante ◽

Daniel Pla ◽

Montserrat Gómez

Keyword(s):

Electron Transfer ◽

Metal Surface ◽

Functional Group ◽

Single Electron ◽

Mechanistic Study ◽

Single Electron Transfer ◽

Palladium Nanoparticle ◽

Transfer Processes ◽

Electron Transfer Processes ◽

Reductive Homocoupling

In this work, we report a palladium nanoparticle-promoted reductive homocoupling of haloarenes, exhibiting a broad functional group tolerance. A mechanistic study was carried out, suggesting single-electron transfer processes on the metal surface.

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