Visible-Light Photosensitized Aryl and Alkyl Decarboxylative Carbon-Heteroatom and Carbon-Carbon Bond Formations

2019 ◽  
Author(s):  
Tuhin Patra ◽  
Satobhisha Mukherjee ◽  
Jiajia Ma ◽  
Felix Strieth-Kalthoff ◽  
Frank Glorius
Keyword(s):  
Energy Transfer ◽  
Visible Light ◽  
Alkyl Radical ◽  
General Strategy ◽  
Alkyl Radicals ◽  
Bond Forming ◽  
Radical Trapping ◽  
Carbon Carbon Bond ◽  
Radical Generation ◽  
Trapping Agent

<sub>A general strategy to access both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters has been developed. An energy transfer mediated homolysis of unsymmetrical sigma-bonds for a concerted fragmentation/decarboxylation process is involved. As a result, an independent aryl/alkyl radical generation step enables a series of key C-X and C-C bond forming reactions by simply changing the radical trapping agent.</sub>

Visible-Light Photosensitized Aryl and Alkyl Decarboxylative Carbon-Heteroatom and Carbon-Carbon Bond Formations

2019 ◽  
Author(s):  
Frank Glorius ◽  
Tuhin Patra ◽  
Satobhisha Mukherjee ◽  
Jiajia Ma ◽  
Felix Strieth-Kalthoff
Keyword(s):  
Energy Transfer ◽  
Visible Light ◽  
Alkyl Radical ◽  
General Strategy ◽  
Alkyl Radicals ◽  
Bond Forming ◽  
Radical Trapping ◽  
Carbon Carbon Bond ◽  
Radical Generation ◽  
Trapping Agent

<sub>A general strategy to access both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters has been developed. An energy transfer mediated homolysis of unsymmetrical sigma-bonds for a concerted fragmentation/decarboxylation process is involved. As a result, an independent aryl/alkyl radical generation step enables a series of key C-X and C-C bond forming reactions by simply changing the radical trapping agent.</sub>

Visible-Light Photosensitized Aryl and Alkyl Decarboxylative Carbon-Heteroatom and Carbon-Carbon Bond Formations

2019 ◽  
Author(s):  
Frank Glorius ◽  
Tuhin Patra ◽  
Satobhisha Mukherjee ◽  
Jiajia Ma ◽  
Felix Strieth-Kalthoff
Keyword(s):  
Energy Transfer ◽  
Visible Light ◽  
Alkyl Radical ◽  
General Strategy ◽  
Alkyl Radicals ◽  
Bond Forming ◽  
Radical Trapping ◽  
Carbon Carbon Bond ◽  
Radical Generation ◽  
Trapping Agent

<sub>A general strategy to access both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters has been developed. An energy transfer mediated homolysis of unsymmetrical sigma-bonds for a concerted fragmentation/decarboxylation process is involved. As a result, an independent aryl/alkyl radical generation step enables a series of key C-X and C-C bond forming reactions by simply changing the radical trapping agent.</sub>

scholarly journals Application of visible-light photosensitization to form alkyl-radical-derived thin films on gold

2017 ◽  
Vol 8 ◽  
pp. 1863-1877 ◽  
Author(s):  
Rashanique D Quarels ◽  
Xianglin Zhai ◽  
Neepa Kuruppu ◽  
Jenny K Hedlund ◽  
Ashley A Ellsworth ◽  
...  
Keyword(s):  
Thin Films ◽  
Visible Light ◽  
Alkyl Radical ◽  
Organic Molecules ◽  
Film Structure ◽  
Small Organic Molecules ◽  
Alkyl Radicals ◽  
Mild Conditions ◽  
Radical Generation ◽  
First Time

Visible-light irradiation of phthalimide esters in the presence of the photosensitizer [Ru(bpy)3]2+ and the stoichiometric reducing agent benzyl nicotinamide results in the formation of alkyl radicals under mild conditions. This approach to radical generation has proven useful for the synthesis of small organic molecules. Herein, we demonstrate for the first time the visible-light photosensitized deposition of robust alkyl thin films on Au surfaces using phthalimide esters as the alkyl radical precursors. In particular, we combine visible-light photosensitization with particle lithography to produce nanostructured thin films, the thickness of which can be measured easily using AFM cursor profiles. Analysis with AFM demonstrated that the films are robust and resistant to mechanical force while contact angle goniometry suggests a multilayered and disordered film structure. Analysis with IRRAS, XPS, and TOF SIMS provides further insights.

ChemInform Abstract: [Cu(dap)2Cl] as an Efficient Visible-Light-Driven Photoredox Catalyst in Carbon-Carbon Bond-Forming Reactions.

ChemInform ◽  
2012 ◽  
Vol 43 (44) ◽  
pp. no-no
Author(s):  
Michael Pirtsch ◽  
Suva Paria ◽  
Taisuke Matsuno ◽  
Hiroyuki Isobe ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Visible Light Driven

scholarly journals Advancements in Visible-Light-Enabled Radical C(sp)2–H Alkylation of (Hetero)arenes

Synthesis ◽  
2019 ◽  
Vol 51 (05) ◽  
pp. 1063-1072 ◽  
Author(s):  
Alexandra Sun ◽  
Rory McAtee ◽  
Edward McClain ◽  
Corey Stephenson
Keyword(s):  
Carboxylic Acid ◽  
Visible Light ◽  
Alkyl Radical ◽  
Functional Group ◽  
Short Review ◽  
Alkyl Halides ◽  
Research Development ◽  
Visible Light Driven ◽  
Radical Generation ◽  
Operational Simplicity

The Minisci reaction, which encompasses the radical C–H alkylation of heteroarenes, has undergone revolutionary development in recent years. The application of photoredox catalysis to alkyl radical generation has given rise to a multitude of methods that feature enhanced functional group tolerance, generality, and operational simplicity. The intent of this short review is to bring readers up to date on this rapidly expanding field. Specifically, we will highlight key examples of visible-light-driven Minisci alkylation strategies that represent key advancements in this area of research. The scope and limitations of these transformations will be discussed, with a focus on examining the underlying pathways for alkyl radical generation. Our goal is to make this short review a stepping stone for further synthetic research development. Sections are organized based on alkyl radical precursor reagents.1 Introduction2 Alkyl Carboxylic Acids and Carboxylic Acid Derivatives3 Alkylboronic Acids4 Potassium Alkyl- and Alkoxymethyltrifluoroborates5 Alkyl Halides6 Alcohols and Ethers7 Conclusion

Visible-light promoted γ-cyanoalkyl radical generation: three-component cyanopropylation/etherification of unactivated alkenes

2017 ◽  
Vol 53 (84) ◽  
pp. 11544-11547 ◽  
Author(s):  
Linyong Li ◽  
Haoguo Chen ◽  
Mingjing Mei ◽  
Lei Zhou
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Alkyl Radicals ◽  
Radical Generation

A photoredox approach to generate distal cyano-substituted alkyl radicals through C–C bond cleavage of cyclobutanone oximes was developed.

[Cu(dap)2Cl] As an Efficient Visible-Light-Driven Photoredox Catalyst in Carbon-Carbon Bond-Forming Reactions

2012 ◽  
Vol 18 (24) ◽  
pp. 7336-7340 ◽  
Author(s):  
Michael Pirtsch ◽  
Suva Paria ◽  
Taisuke Matsuno ◽  
Hiroyuki Isobe ◽  
Oliver Reiser
Keyword(s):  
Visible Light ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Visible Light Driven
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