Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Chan, Amy Y.; Perry, Ian B.; Bissonnette, Noah B.; Buksh, Benito F.; Edwards, Grant A.; Frye, Lucas I.; Garry, Olivia L.; Lavagnino, Marissa N.; Li, Beryl X.; Liang, Yufan; Mao, Edna; Millet, Agustin; Oakley, James V.; Reed, Nicholas L.; Sakai, Holt A.; Seath, Ciaran P.; MacMillan, David C.

doi:10.1021/acs.chemrev.1c00383

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Journal Article · Thu Nov 18 00:00:00 EST 2021 · Chemical Reviews

DOI:https://doi.org/10.1021/acs.chemrev.1c00383· OSTI ID:2281322

Chan, Amy Y. ^[1]; Perry, Ian B. ^[2]; ^[2]; Buksh, Benito F. ^[2]; Edwards, Grant A. ^[2]; ^[2]; Garry, Olivia L. ^[2]; ^[2]; Li, Beryl X. ^[2]; Liang, Yufan ^[2]; Mao, Edna ^[2]; Millet, Agustin ^[2]; Oakley, James V. ^[2]; ^[2]; Sakai, Holt A. ^[2]; Seath, Ciaran P. ^[2]; ^[2]

Princeton Univ., NJ (United States). Merck Center for Catalysis; Princeton University
Princeton Univ., NJ (United States). Merck Center for Catalysis

The merger of photoredox catalysis with transition metal catalysis, termed metallaphotoredox catalysis, has become a mainstay in synthetic methodology over the past decade. Metallaphotoredox catalysis has combined the unparalleled capacity of transition metal catalysis for bond formation with the broad utility of photoinduced electron- and energy-transfer processes. Photocatalytic substrate activation has allowed the engagement of simple starting materials in metal-mediated bond-forming processes. Moreover, electron or energy transfer directly with key organometallic intermediates has provided novel activation modes entirely complementary to traditional catalytic platforms. Finally, this Review details and contextualizes the advancements in molecule construction brought forth by metallaphotocatalysis.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Bio-inspired Light-Escalated Chemistry (BioLEC); Princeton Univ., NJ (United States)

Sponsoring Organization:: National Institute of General Medical Sciences (NIGMS); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0019370

OSTI ID:: 2281322

Alternate ID(s):: OSTI ID: 1977812

Journal Information:: Chemical Reviews, Journal Name: Chemical Reviews Journal Issue: 2 Vol. 122; ISSN 0009-2665

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Dual Catalytic Strategy for Forging sp ² – sp ³ and sp ³ – sp ³ Architectures via β - Scission of Aliphatic Alcohol Derivatives Cong, Fei; Lv, Xin-Yang; Day, Craig S. Journal of the American Chemical Society, Vol. 142, Issue 49 https://doi.org/10.1021/jacs.0c11172	journal	November 2020
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Photocatalytic Dehydroxymethylative Arylation by Synergistic Cerium and Nickel Catalysis Chen, Yuegang; Wang, Xin; He, Xu Journal of the American Chemical Society, Vol. 143, Issue 13 https://doi.org/10.1021/jacs.1c00618	journal	March 2021
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Aromatic Methoxylation and Hydroxylation by Organometallic High-Valent Nickel Complexes Zhou, Wen; Schultz, Jason W.; Rath, Nigam P. Journal of the American Chemical Society, Vol. 137, Issue 24 https://doi.org/10.1021/jacs.5b04082	journal	June 2015
Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis Tasker, Sarah Z.; Jamison, Timothy F. Journal of the American Chemical Society, Vol. 137, Issue 30 https://doi.org/10.1021/jacs.5b05597	journal	July 2015
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Photocatalytic Hydrogen-Evolution Cross-Couplings: Benzene C–H Amination and Hydroxylation Zheng, Yi-Wen; Chen, Bin; Ye, Pan Journal of the American Chemical Society, Vol. 138, Issue 32 https://doi.org/10.1021/jacs.6b05498	journal	August 2016
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Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C≡C Triple Bond Cleavage Sagadevan, Arunachalam; Charpe, Vaibhav Pramod; Ragupathi, Ayyakkannu Journal of the American Chemical Society, Vol. 139, Issue 8 https://doi.org/10.1021/jacs.6b13113	journal	February 2017
Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C–N Bond Activation Basch, Corey H.; Liao, Jennie; Xu, Jianyu Journal of the American Chemical Society, Vol. 139, Issue 15 https://doi.org/10.1021/jacs.7b02389	journal	April 2017
Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions Huang, Xiaoqiang; Quinn, Taylor R.; Harms, Klaus Journal of the American Chemical Society, Vol. 139, Issue 27 https://doi.org/10.1021/jacs.7b04363	journal	June 2017
Visible-Light-Driven Carboxylation of Aryl Halides by the Combined Use of Palladium and Photoredox Catalysts Shimomaki, Katsuya; Murata, Kei; Martin, Ruben Journal of the American Chemical Society, Vol. 139, Issue 28 https://doi.org/10.1021/jacs.7b04838	journal	July 2017
Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer Primer, David N.; Molander, Gary A. Journal of the American Chemical Society, Vol. 139, Issue 29 https://doi.org/10.1021/jacs.7b06288	journal	July 2017
Direct Aldehyde C–H Arylation and Alkylation via the Combination of Nickel, Hydrogen Atom Transfer, and Photoredox Catalysis Zhang, Xiaheng; MacMillan, David W. C. Journal of the American Chemical Society, Vol. 139, Issue 33 https://doi.org/10.1021/jacs.7b07078	journal	August 2017
Photoinduced, Copper-Catalyzed Decarboxylative C–N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement Zhao, Wei; Wurz, Ryan P.; Peters, Jonas C. Journal of the American Chemical Society, Vol. 139, Issue 35 https://doi.org/10.1021/jacs.7b07546	journal	August 2017
Photoinduced Nickel-Catalyzed Chemo- and Regioselective Hydroalkylation of Internal Alkynes with Ether and Amide α-Hetero C(sp ³ )–H Bonds Deng, Hong-Ping; Fan, Xuan-Zi; Chen, Zhi-Hui Journal of the American Chemical Society, Vol. 139, Issue 38 https://doi.org/10.1021/jacs.7b08158	journal	September 2017
Visible-Light-Activated Asymmetric β-C–H Functionalization of Acceptor-Substituted Ketones with 1,2-Dicarbonyl Compounds Ma, Jiajia; Rosales, Anthony R.; Huang, Xiaoqiang Journal of the American Chemical Society, Vol. 139, Issue 48 https://doi.org/10.1021/jacs.7b09152	journal	November 2017
A Mild Hydroaminoalkylation of Conjugated Dienes Using a Unified Cobalt and Photoredox Catalytic System Thullen, Scott M.; Rovis, Tomislav Journal of the American Chemical Society, Vol. 139, Issue 43 https://doi.org/10.1021/jacs.7b09252	journal	October 2017
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Enantioselective Decarboxylative Cyanation Employing Cooperative Photoredox Catalysis and Copper Catalysis Wang, Dinghai; Zhu, Na; Chen, Pinhong Journal of the American Chemical Society, Vol. 139, Issue 44 https://doi.org/10.1021/jacs.7b09802	journal	October 2017
Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N -Alkylation Reactions of Unactivated Secondary Halides Ahn, Jun Myun; Peters, Jonas C.; Fu, Gregory C. Journal of the American Chemical Society, Vol. 139, Issue 49 https://doi.org/10.1021/jacs.7b10907	journal	November 2017
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