Metallaphotoredox Catalysis for Multicomponent Coupling Reactions

2021 ◽  
Author(s):  
Wen-Jing Xiao ◽  
Fu-Dong Lu ◽  
Gui-Feng He ◽  
Liang-Qiu Lu
Keyword(s):  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Coupling Reactions ◽  
Complex Molecules ◽  
Metal Catalysis ◽  
Mild Conditions ◽  
Multicomponent Coupling Reactions ◽  
Multicomponent Coupling

The combination of photoredox and transition metal catalysis, which is termed metallaphotoredox catalysis, is a powerful platform for building complex molecules under mild conditions. In particular, metallaphotoredox-catalyzed multicomponent coupling reactions,...

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.

Transition-metal-catalyzed multicomponent coupling reactions with imines and carbon monoxide

2013 ◽  
Vol 85 (2) ◽  
pp. 377-384 ◽  
Author(s):  
Jeffrey S. Quesnel ◽  
Bruce A. Arndtsen
Keyword(s):  
Transition Metal ◽  
Building Blocks ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Heterocyclic Derivatives ◽  
One Step ◽  
Multicomponent Coupling Reactions ◽  
Metal Catalyzed ◽  
And Control ◽  
Multicomponent Coupling

Multicomponent coupling reactions provide a method to combine several substrates in a single reaction. When coupled with transition-metal catalysis, these reactions can be used to both activate and control the assembly of multiple simple building blocks directly into useful products. This account will describe our work in this area, with a focus on the use of palladium catalysis as a tool to couple imines and CO with other substrates into a range of heterocyclic derivatives in one-step reactions.

Organocatalytic Atom-Transfer C(sp3)–H Oxidation

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2331-2336 ◽  
Author(s):  
Michael Hilinski ◽  
Shea Johnson ◽  
Logan Combee
Keyword(s):  
Transition Metal ◽  
Late Stage ◽  
Transition Metal Catalysis ◽  
Great Promise ◽  
Atom Transfer ◽  
Complex Molecules ◽  
Metal Catalysis ◽  
Iminium Salt ◽  
Site Selective

Predictably site-selective catalytic methods for intermolecular C(sp3)–H hydroxylation and amination hold great promise for the synthesis and late-stage modification of complex molecules. Transition-metal catalysis has been the most common approach for early investigations of this type of reaction. In comparison, there are far fewer ­reports of organocatalytic methods for direct oxygen or nitrogen insertion into C–H bonds. Herein, we provide an overview of early efforts in this area, with particular emphasis on our own recent development of an iminium salt that catalyzes both oxygen and nitrogen insertion.1 Introduction2 Background: C–H Oxidation Capabilities of Heterocyclic Oxidants3 Oxaziridine-Mediated Catalytic Hydroxylation4 Dioxirane-Mediated Catalytic Hydroxylation5 Iminium Salt Catalysis of Hydroxylation and Amination6 Conclusion and Outlook

scholarly journals N-Tosylcarboxamide in C–H Functionalization: More than a Simple Directing Group

Processes ◽  
2020 ◽  
Vol 8 (8) ◽  
pp. 981
Author(s):  
Benjamin Large ◽  
Vincent Terrasson ◽  
Damien Prim
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Organic Synthesis ◽  
Transition Metal Catalysis ◽  
Ortho Position ◽  
Aromatic Rings ◽  
One Pot ◽  
Complex Molecules ◽  
Metal Catalysis ◽  
Directing Group

C–H activation with transition metal catalysis has become an important tool in organic synthesis for the functionalization of low reactive bonds and the preparation of complex molecules. The choice of the directing group (DG) proves to be crucial for the selectivity in this type of reaction, and several different functional groups have been used efficiently. This review describes recent advances in C–H functionalization of aromatic rings directed by a N-tosylcarboxamide group. Results regarding alkenylation, alkoxylation, halogenation, and arylation of C–H in the ortho position to the tosylcarboxamide are presented. Moreover, the advantage of this particular directing group is that it can undergo further transformation and act as CO or CON fragment reservoir to produce, in sequential fashion or one-pot sequence, various interesting (hetero)cycles such as phenanthridinones, dihydroisoquinolinones, fluorenones, or isoindolinones.

scholarly journals Transition-Metal-Free Synthesis of Conjugated Microporous Polymers via Amine-Catalyzed Suzuki-Miyaura Coupling Reaction

2021 ◽  
Author(s):  
Qingmin Liu ◽  
Shangbin Jin ◽  
Bien Tan
Keyword(s):  
Transition Metal ◽  
Noble Metal ◽  
Coupling Reaction ◽  
Transition Metal Catalysis ◽  
Coupling Reactions ◽  
Metal Catalysis ◽  
Metal Free ◽  
Noble Metal Catalysts ◽  
Microporous Polymers ◽  
Conjugated Microporous Polymers

The synthesis of conjugated microporous polymers (CMPs) has been heavily relied on transition-metal-catalysis carbon-carbon coupling reactions, which has shortages in the scarcity and high cost of the noble metal catalysts....

scholarly journals Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms

2014 ◽  
Vol 43 (13) ◽  
pp. 4368-4380 ◽  
Author(s):  
Hee Yeon Cho ◽  
James P. Morken
Keyword(s):  
Transition Metal ◽  
Functional Groups ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Coupling Reactions ◽  
Multicomponent Coupling Reactions ◽  
Multicomponent Coupling

This review covers the bis-metallative coupling of unsaturated functional groups under the agency of transition metal catalysts.

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