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 Asymmetric Catalysis by Chiral Complexes of First-Row Transition Metals

Synthesis ◽  
2020 ◽  
Author(s):  
Yanjun Li ◽  
Ziqi Ye ◽  
Jiaxin Cai ◽  
Lei Gong
Keyword(s):  
Transition Metals ◽  
Visible Light ◽  
Asymmetric Catalysis ◽  
Functional Group ◽  
Short Review ◽  
Chiral Complexes ◽  
Diverse Range ◽  
Mild Conditions ◽  
Nickel Cobalt ◽  
Visible Light Driven

This short review presents an overview of visible-light-driven asymmetric catalysis by chiral complexes of first-row transition metals. The processes described here include dual catalysis by a chiral complex of copper, nickel, cobalt or chromium and an additional photoredox or energy-transfer catalyst, and bifunctional catalysis by a single chiral copper or nickel catalyst. These methods allow valuable transformations with high functional group compatibility. They provide stereoselective construction of carbon-carbon or carbon-heteroatom bonds under mild conditions, and produce a diverse range of previously unknown enantio-enriched compounds.

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-mediated borylation of aryl and alkyl halides with a palladium complex

2020 ◽  
Vol 18 (23) ◽  
pp. 4390-4394
Author(s):  
Jia-Hui Zhao ◽  
Zhao-Zhao Zhou ◽  
Yue Zhang ◽  
Xuan Su ◽  
Xi-Meng Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Palladium Complex ◽  
Alkyl Halides ◽  
Palladium Catalyzed ◽  
High Yields

Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility.

scholarly journals Visible Light-Mediated [2+2] Cycloaddition for the Synthesis of Azetidines via Energy Transfer

2018 ◽  
Author(s):  
Marc R. Becker ◽  
Alistair D. Richardson ◽  
Corinna S. Schindler
Keyword(s):  
Energy Transfer ◽  
Visible Light ◽  
Functional Group ◽  
Transfer Mechanism ◽  
Synthetic Methods ◽  
Energy Transfer Mechanism ◽  
Triplet Energy ◽  
Mechanistic Investigations ◽  
Triplet Energy Transfer ◽  
Operational Simplicity

<p>Due to the lack of synthetic methods for their synthesis, azetidines are an underrepresented class of nitrogen-containing heterocycles. Herein, we describe the development of a mild, general protocol for the synthesis of azetidines relying on a visible light-mediated [2+2] cycloaddition between oximes and olefins catalyzed by an iridium photocatalyst. This approach is characterized by its operational simplicity, low catalyst loadings and functional group tolerance. Mechanistic investigations suggest that a triplet energy transfer mechanism is operative.<br></p>

Visible-Light-Driven Reductive Carboarylation of Styrenes with CO2 and Aryl Halides

2019 ◽  
Author(s):  
Hao Wang ◽  
yuzhen gao ◽  
Chunlin Zhou ◽  
Gang Li
Keyword(s):  
Visible Light ◽  
Alkyl Halides ◽  
Aryl Halides ◽  
Addition Reactions ◽  
Aryl Chlorides ◽  
Aryl Iodides ◽  
Visible Light Driven ◽  
User Friendly

The first example of visible-light-driven reductive carboarylation of styrenes with CO<sub>2</sub> and aryl halides in a regioselective manner has been achieved. A broad range of aryl iodides and bromides were compatible with this reaction. <a>Moreover, pyridyl halides, alkyl halides and even aryl chlorides were also viable with this method.</a> These findings may stimulate the exploration of novel visible-light-driven Meerwein arylation-addition reactions with user-friendly aryl halides as the radical sources and the photocatalytic utilization of CO<sub>2.</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>

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene derivatives for C(sp3)–C(sp) bond formation catalyzed by a B12 complex

2019 ◽  
Vol 55 (87) ◽  
pp. 13070-13073 ◽  
Author(s):  
Li Chen ◽  
Yohei Kametani ◽  
Kenji Imamura ◽  
Tsukasa Abe ◽  
Yoshihito Shiota ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Visible Light Driven

Visible light-driven cross-coupling reactions of alkyl halides with phenylacetylene and its derivatives catalyzed by the cobalamin derivative (B12) with the [Ir(dtbbpy)(ppy)2]PF6 photocatalyst at room temperature are reported.

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