A Photophysical Study of Sensitization-Initiated Electron Transfer: Insights into the Mechanism of Photoredox Activity

被引：52

作者：

Coles, Max S. ^{[1
]}

Quach, Gina ^{[1
]}

Beves, Jonathon E. ^{[2
]}

Moore, Evan G. ^{[1
]}

机构：

[1] Univ Queensland, Sch Chem & Mol Biosci, Brisbane, Qld 4072, Australia

[2] Univ New South Wales, Sch Chem, Sydney, NSW 2052, Australia

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 24期

基金：

澳大利亚研究理事会;

关键词：

absorption spectroscopy; catalysis; photoredox chemistry; reaction mechanisms; sensitization-initiated electron transfer; GEMINATE RECOMBINATION; TRANSIENT ABSORPTION; EXCITED-STATE; FEMTOSECOND; CATALYSIS; PYRENE;

D O I：

10.1002/anie.201916359

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The development of photocatalytic reactions has provided many novel opportunities to expand the scope of synthetic organic chemistry. In parallel with progress towards uncovering new reactivity, there is consensus that efforts focused on providing detailed mechanistic insight in order to uncover underlying excited-state reactions are essential to maximise formation of desired products. With this in mind, we have investigated the recently reported sensitization-initiated electron transfer (SenI-ET) reaction for the C-H arylation of activated aryl halides. Using a variety of techniques, and in particular nanosecond transient absorption spectroscopy, we are able to distinguish several characteristic signals from the excited-state species involved in the reaction, and subsequent kinetic analysis under various conditions has facilitated a detailed insight into the likely reaction mechanism.

引用

页码：9522 / 9526

页数：5

共 30 条

[1] The photophysics of photoredox catalysis: a roadmap for catalyst design [J].

Arias-Rotondo, Daniela M. ;

McCusker, James K. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (21) :5803-5820

[2] Photochemistry and photocatalysis [J].

Balzani, Vincenzo ;

Bergamini, Giacomo ;

Ceroni, Paola .

RENDICONTI LINCEI-SCIENZE FISICHE E NATURALI, 2017, 28 :125-142

[3]

Buzzetti L., 2019, ANGEW CHEM, V131, P3768, DOI [DOI 10.1002/ANGE.201809984, 10.1002/ange.201809984]

[4] Mechanistic Studies in Photocatalysis [J].

Buzzetti, Luca ;

Crisenza, Giacomo E. M. ;

Melchiorre, Paolo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) :3730-3747

[5]

Chatterjee A., 2019, Angew Chem, V131, P14427, DOI DOI 10.1002/ANGE.201905485

[6] Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer [J].

Chatterjee, Anamitra ;

Koenig, Burkhard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) :14289-14294

[7] Ion-pairing control of excited-state electron-transfer reactions. Quenching, charge recombination, and back electron transfer [J].

Clark, CD ;

Hoffman, MZ .

JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (18) :7526-7532

[8] The Tandem Photoredox Catalysis Mechanism of [Ir(ppy)2(dtb-bpy)]+ Enabling Access to Energy Demanding Organic Substrates [J].

Connell, Timothy U. ;

Fraser, Catherine L. ;

Czyz, Milena L. ;

Smith, Zoe M. ;

Hayne, David J. ;

Doeven, Egan H. ;

Agugiaro, Johnny ;

Wilson, David J. D. ;

Adcock, Jacqui L. ;

Scully, Andrew D. ;

Gomez, Daniel E. ;

Barnett, Neil W. ;

Polyzos, Anastasios ;

Francis, Paul S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (44) :17646-17658

[9] ELECTRON-TRANSFER REACTIONS OF EXCITED-STATES - DIRECT EVIDENCE FOR REDUCTION OF CHARGE-TRANSFER EXCITED-STATE OF TRIS(2,2'-BIPYRIDINE)RUTHENIUM(II) [J].

CREUTZ, C ;

SUTIN, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (20) :6384-6385

[10] Discovery and Elucidation of Counteranion Dependence in Photoredox Catalysis [J].

Farney, Elliot P. ;

Chapman, Steven J. ;

Swords, Wesley B. ;

Torelli, Marco D. ;

Hamers, Robert J. ;

Yoon, Tehshik P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (15) :6385-6391

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