Visible‐Light‐Mediated Cross‐Couplings and C−H Activation via Dual Photoredox/Transition‐Metal Catalysis in Continuous‐Flow Processes

2019 ◽  
Vol 8 (9) ◽  
pp. 1578-1587 ◽  
Author(s):  
Soo Dong Kim ◽  
Jonghyun Lee ◽  
Nam‐Jung Kim ◽  
Boyoung Y. Park
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Continuous Flow ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Flow Processes

Visible Light-Induced Transition Metal Catalysis

2021 ◽  
Author(s):  
Kelvin Pak Shing Cheung ◽  
Sumon Sarkar ◽  
Vladimir Gevorgyan
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

scholarly journals TiO2 Photocatalyzed C–H Bond Transformation for C–C Coupling Reactions

Catalysts ◽  
2018 ◽  
Vol 8 (9) ◽  
pp. 355 ◽  
Author(s):  
Yi Wang ◽  
Anan Liu ◽  
Dongge Ma ◽  
Shuhong Li ◽  
Chichong Lu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Transition Metal Catalysis ◽  
Light Irradiation ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Bond Functionalization ◽  
Tio2 Photocatalysis ◽  
Mild Conditions

Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction of the synthetic steps required for substrate prefunctionalization such as halogenation, borylation, and metalation. Successful C–H bond functionalization mainly resorts to homogeneous transition-metal catalysis, albeit sometimes suffering from poor catalyst reusability, nontrivial separation, and severe biotoxicity. TiO2 photocatalysis displays multifaceted advantages, such as strong oxidizing ability, high chemical stability and photostability, excellent reusability, and low biotoxicity. The chemical reactions started and delivered by TiO2 photocatalysts are well known to be widely used in photocatalytic water-splitting, organic pollutant degradation, and dye-sensitized solar cells. Recently, TiO2 photocatalysis has been demonstrated to possess the unanticipated ability to trigger the transformation of inert C–H bonds for C–C, C–N, C–O, and C–X bond formation under ultraviolet light, sunlight, and even visible-light irradiation at room temperature. A few important organic products, traditionally synthesized in harsh reaction conditions and with specially functionalized group substrates, are continuously reported to be realized by TiO2 photocatalysis with simple starting materials under very mild conditions. This prominent advantage—the capability of utilizing cheap and readily available compounds for highly selective synthesis without prefunctionalized reactants such as organic halides, boronates, silanes, etc.—is attributed to the overwhelmingly powerful photo-induced hole reactivity of TiO2 photocatalysis, which does not require an elevated reaction temperature as in conventional transition-metal catalysis. Such a reaction mechanism, under typically mild conditions, is apparently different from traditional transition-metal catalysis and beyond our insights into the driving forces that transform the C–H bond for C–C bond coupling reactions. This review gives a summary of the recent progress of TiO2 photocatalytic C–H bond activation for C–C coupling reactions and discusses some model examples, especially under visible-light irradiation.

scholarly journals The A3 Redox-Neutral C1-Alkynylation of Tetrahydroisoquinolines: A Comparative Study between Visible Light Photocatalysis and Transition-Metal Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Vladimir V. Kouznetsov ◽  
Marlyn C. Ortiz Villamizar ◽  
Carlos E. Puerto Galvis
Keyword(s):  
Transition Metal ◽  
Microwave Irradiation ◽  
Visible Light ◽  
High Selectivity ◽  
Transition Metal Catalysis ◽  
Visible Light Photocatalysis ◽  
Reaction Conditions ◽  
Metal Catalysis ◽  
New Compounds ◽  
Optimal Reaction

AbstractConsidering the current challenges of the A3 redox-neutral C1-alkynylation of tetrahydroisoquinolines (THIQs), we studied this synthetic tool under visible light photocatalysis and transition-metal catalysis in order to describe alternative reaction conditions and discuss possible improvements to this process. We demonstrated that 1-alkynylated THIQs can be readily obtained by three different approaches: iridium-based photocatalysis and copper ([CuBr(PPh3)3]) and silver (AgNO3) catalysis under mild, selective and accessible reaction conditions. Among these approaches, the copper(I)-based methodology resulted in the most robust, optimal reaction conditions for the synthesis of a series of 18 1-alkynylated THIQs in moderate to excellent yields and with high selectivity for the endo-alkynylated products. Moreover, this reaction can be accelerated by microwave irradiation (120 °C, 15 min) affording a novel library of diverse THIQs with alkyne and N-substituent moieties, from unreactive and uncommon substrates, that could be further transformed into new compounds of interest.

Combining Visible Light Catalysis and Transition Metal Catalysis for the Alkylation of Secondary Amines

2013 ◽  
Vol 355 (11-12) ◽  
pp. 2158-2164 ◽  
Author(s):  
Xue-Wang Gao ◽  
Qing-Yuan Meng ◽  
Ming Xiang ◽  
Bin Chen ◽  
Ke Feng ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Transition Metal Catalysis ◽  
Secondary Amines ◽  
Metal Catalysis

1.2.1 General Principles of Transition-Metal/Photocatalyst Dual Catalysis

2020 ◽  
Author(s):  
J. C. Tellis
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Transition Metal Catalysis ◽  
Specific Role ◽  
Visible Light Photocatalysis ◽  
Metal Catalysis ◽  
Catalytic Transformations ◽  
Dual Catalysis

AbstractThe combination of transition-metal catalysis and visible-light photocatalysis offers opportunities for the development of unique new forms of reactivity. Presented in this chapter is an overview of the various strategies that can be used to design these dual catalytic transformations. Emphasis is placed on understanding the specific role that a photocatalyst can play in augmenting the reactivity of a substrate or cocatalyst to achieve otherwise challenging transformations.

scholarly journals Visible Light-Induced Excited-State Transition-Metal Catalysis

2019 ◽  
Vol 1 (5) ◽  
pp. 510-523 ◽  
Author(s):  
Rajesh Kancherla ◽  
Krishnamoorthy Muralirajan ◽  
Arunachalam Sagadevan ◽  
Magnus Rueping
Keyword(s):  
Excited State ◽  
Transition Metal ◽  
Visible Light ◽  
State Transition ◽  
Transition Metal Catalysis ◽  
Metal Catalysis

Homogeneous visible light mediated transition metal catalysis other than Ruthenium and Iridium

2019 ◽  
Vol 4 (7) ◽  
Author(s):  
Lukas Traub ◽  
Oliver Reiser
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Metal Complexes ◽  
Coordination Compounds ◽  
Organic Dyes ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Iron Nickel ◽  
Efficient Alternative ◽  
Cost Efficient

Abstract The field of photoredox chemistry is dominated by ruthenium- or iridium based metal complexes or organic dyes that are employed as catalysts. Other metal based coordination compounds provide a cost efficient alternative, however, the much shorter excited lifetimes generally observed for such complexes make their application more challenging. Nevertheless, a growing number of successful examples with metal complexes based on chromium, iron, nickel, zirconium, cerium, rhenium, platinum, uranium, and especially on copper exist, which is being reviewed in this chapter.

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