ChemInform Abstract: Preparative Semiconductor Photoredox Catalysis: An Emerging Theme in Organic Synthesis

ChemInform ◽  
2016 ◽  
Vol 47 (12) ◽  
pp. no-no
Author(s):  
David W. Manley ◽  
John C. Walton
Keyword(s):  
Organic Synthesis ◽  
Photoredox Catalysis

Visible light photocatalysis in synthesis of pharmaceutically relevant heterocyclic scaffolds

2022 ◽  
Author(s):  
Vishal Srivastava ◽  
Pravin Kumar Singh ◽  
Shraddha Tivari ◽  
Praveen Pratap Singh
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Chemical Bond ◽  
Organic Synthesis ◽  
Bond Formation ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Chemical Bond Formation

Visible light and photoredox catalysis have emerged as a powerful and long-lasting tool for organic synthesis, demonstrating the importance of a variety of chemical bond formation methods. Natural products, physiologically...

Excited radical anions and excited anions in visible light photoredox catalysis

2019 ◽  
Vol 4 (12) ◽  
Author(s):  
Indrajit Ghosh
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Transition Metal Complexes ◽  
Organic Dyes ◽  
Visible Light Photocatalysis ◽  
Radical Anions ◽  
Photoredox Catalysis ◽  
Inorganic Semiconductors ◽  
Redox Active ◽  
Excited Radical

Abstract Over the last decade, visible light photocatalysis has dramatically increased the arsenal of methods for organic synthesis and changed the way we activate molecules for chemical reactions. Polypyridyl transition metal complexes, redox-active organic dyes, and inorganic semiconductors are typically used as photocatalysts for such transformations. This chapter reviews the applications of radical anions and anions as photosensitizers in visible light photoredox catalysis.

scholarly journals Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

2018 ◽  
Vol 14 ◽  
pp. 1215-1221 ◽  
Author(s):  
Yue Pan ◽  
Kunfang Jia ◽  
Yali Chen ◽  
Yiyun Chen
Keyword(s):  
Organic Synthesis ◽  
Photoredox Catalysis ◽  
Radical Acceptor ◽  
First Time

The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the radical acceptor and oxidative quencher reactivity of alkynylbenziodoxoles, in which unsubstituted alkynylbenziodoxoles played balancing roles in both processes, while electron-rich benziodoxole derivatives demonstrate synthetic advantages in some cases.

ChemInform Abstract: Visible Light Photoredox Catalysis: Applications in Organic Synthesis

ChemInform ◽  
2011 ◽  
Vol 42 (19) ◽  
pp. no-no
Author(s):  
Jagan M. R. Narayanam ◽  
Corey R. J. Stephenson
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Photoredox Catalysis

scholarly journals Asymmetric benzylic C(sp3)−H acylation via dual nickel and photoredox catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Leitao Huan ◽  
Xiaomin Shu ◽  
Weisai Zu ◽  
De Zhong ◽  
Haohua Huo
Keyword(s):  
Carboxylic Acids ◽  
Organic Synthesis ◽  
Late Stage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Cross Coupling Reaction ◽  
Aryl Ketones ◽  
Alkyl Benzenes

AbstractAsymmetric C(sp3)−H functionalization is a persistent challenge in organic synthesis. Here, we report an asymmetric benzylic C−H acylation of alkylarenes employing carboxylic acids as acyl surrogates for the synthesis of α-aryl ketones via nickel and photoredox dual catalysis. This mild yet straightforward protocol transforms a diverse array of feedstock carboxylic acids and simple alkyl benzenes into highly valuable α-aryl ketones with high enantioselectivities. The utility of this method is showcased in the gram-scale synthesis and late-stage modification of medicinally relevant molecules. Mechanistic studies suggest a photocatalytically generated bromine radical can perform benzylic C−H cleavage to activate alkylarenes as nucleophilic coupling partners which can then engage in a nickel-catalyzed asymmetric acyl cross-coupling reaction. This bromine-radical-mediated C−H activation strategy can be also applied to the enantioselective coupling of alkylarenes with chloroformate for the synthesis of chiral α-aryl esters.

scholarly journals Preparative semiconductor photoredox catalysis: An emerging theme in organic synthesis

2015 ◽  
Vol 11 ◽  
pp. 1570-1582 ◽  
Author(s):  
David W Manley ◽  
John C Walton
Keyword(s):  
Organic Synthesis ◽  
Radical Anion ◽  
Radical Cations ◽  
Aromatic Aldehydes ◽  
Hydrogen Gas ◽  
Primary Amines ◽  
Tertiary Amines ◽  
Photoredox Catalysis ◽  
Enol Ethers ◽  
Cyclic Amines

Heterogeneous semiconductor photoredox catalysis (SCPC), particularly with TiO2, is evolving to provide radically new synthetic applications. In this review we describe how photoactivated SCPCs can either (i) interact with a precursor that donates an electron to the semiconductor thus generating a radical cation; or (ii) interact with an acceptor precursor that picks up an electron with production of a radical anion. The radical cations of appropriate donors convert to neutral radicals usually by loss of a proton. The most efficient donors for synthetic purposes contain adjacent functional groups such that the neutral radicals are resonance stabilized. Thus, ET from allylic alkenes and enol ethers generated allyl type radicals that reacted with 1,2-diazine or imine co-reactants to yield functionalized hydrazones or benzylanilines. SCPC with tertiary amines enabled electron-deficient alkenes to be alkylated and furoquinolinones to be accessed. Primary amines on their own led to self-reactions involving C–N coupling and, with terminal diamines, cyclic amines were produced. Carboxylic acids were particularly fruitful affording C-centered radicals that alkylated alkenes and took part in tandem addition cyclizations producing chromenopyrroles; decarboxylative homo-dimerizations were also observed. Acceptors initially yielding radical anions included nitroaromatics and aromatic iodides. The latter led to hydrodehalogenations and cyclizations with suitable precursors. Reductive SCPC also enabled electron-deficient alkenes and aromatic aldehydes to be hydrogenated without the need for hydrogen gas.

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