Visible-light-induced dual C–C bond formation via selective C(sp3)–H bond cleavage: efficient access to alkylated oxindoles from activated alkenes and simple ethers under metal-free conditions

2017 ◽  
Vol 19 (7) ◽  
pp. 1732-1739 ◽  
Author(s):  
Dong Xia ◽  
Yang Li ◽  
Tao Miao ◽  
Pinhua Li ◽  
Lei Wang
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Metal Free ◽  
Efficient Access ◽  
Oxidative Difunctionalization

A visible-light-induced oxidative difunctionalization of activated alkenes with simple ethersviaselective C(sp3)–H bond cleavage and dual C–C bond formation was developed.

Stepwise photosensitized C(sp3)–C(CO) bond cleavage and C–P bond formation of 1,3-dicarbonyls with arylphosphine oxides

2019 ◽  
Vol 6 (9) ◽  
pp. 1433-1437 ◽  
Author(s):  
Xiuli Zhao ◽  
Mengmeng Huang ◽  
Yabo Li ◽  
Jianye Zhang ◽  
Jung Keun Kim ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Radical Reaction ◽  
Metal Free

A visible-light-induced metal-free cascade radical reaction of chemoselective C–C bond cleavage with a C–P bond formation was discovered to obtain β-ketophosphine oxides.

scholarly journals Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

2019 ◽  
Vol 10 (6) ◽  
pp. 1687-1691 ◽  
Author(s):  
Mrinmoy Das ◽  
Minh Duy Vu ◽  
Qi Zhang ◽  
Xue-Wei Liu
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Formation Processes ◽  
New Approach ◽  
Carbon Bond ◽  
Metal Free ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
New Strategy

Phosphonium ylides have shown their synthetic usefulness in important carbon–carbon bond formation processes. Our new strategy employs phosphonium ylides as novel carbyne equivalents and features a new approach for constructing carbon–carbon bonds from alkenes.

DDQ-mediated regioselective C–S bond formation: efficient access to allylic sulfides

2018 ◽  
Vol 5 (21) ◽  
pp. 3158-3162 ◽  
Author(s):  
Chunsheng Li ◽  
Jianxiao Li ◽  
Chaowei Tan ◽  
Wanqing Wu ◽  
Huanfeng Jiang
Keyword(s):  
Bond Formation ◽  
Metal Free ◽  
Efficient Access

A novel metal-free dehydrocoupling approach for constructing allylic sulfides via oxidative allylic C–H functionalization with high atom- and step-economy has been developed.

I2/TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C–C Bond Cleavage

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 2018-2023 ◽  
Author(s):  
Xiang Fang ◽  
Xueyan Yang ◽  
Tongle Shao ◽  
Jun Zhou ◽  
Chen Jin ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Oxidation Pathway ◽  
Keto Esters ◽  
Oxidative Coupling Reaction

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I2/TBHP promoted sequential iodination, C–C bond cleavage, C–O bond formation and oxidation pathway is involved in this reaction.

Photoinduced Oxidative Cross-Coupling for O–S Bond Formation: A Facile Synthesis of Alkyl Benzenesulfonates

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1558-1563 ◽  
Author(s):  
Aiwen Lei ◽  
Atul Singh ◽  
Hong Yi ◽  
Guoting Zhang ◽  
Changliang Bian ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Cross Coupling ◽  
Selective Synthesis ◽  
Mechanistic Studies ◽  
Facile Synthesis ◽  
Metal Free

We have developed a photoinduced oxidative cross-coupling of thiophenols with alcohols for O–S bond formation. The protocol uses visible light, a metal-free photocatalyst, and oxygen as the oxidant for the selective synthesis of alkyl benzenesulfonates; no ligand co-additive is necessary. Mechanistic studies suggested that the disulfide and alkyl benzenesulfinate are involved as intermediates and that the transformation proceeds by a radical pathway.

Metal-free desilylative C–C bond formation by visible-light photoredox catalysis

2019 ◽  
Vol 55 (20) ◽  
pp. 2980-2983 ◽  
Author(s):  
Mustafa Uygur ◽  
Tobias Danelzik ◽  
Olga García Mancheño
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Photoredox Catalysis ◽  
Metal Free

A novel metal-free desilylative C–C bond formation from simple organosilanes by visible-light acridinium photoredox catalysis is presented.

scholarly journals Photoinduced Deaminative Borylation of Unactivated Aromatic Amines Enhanced by CO2

2021 ◽  
Author(s):  
Akira Shiozuka ◽  
Kohei Sekine ◽  
Yoichiro Kuninobu
Keyword(s):  
Aromatic Amines ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Inhibitory Effect ◽  
Light Irradiation ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Stoichiometric Amount ◽  
Optimal Reaction

Herein, direct unactivated C-N borylation of aromatic amines by a photocatalyst was achieved under mild and metal-free conditions. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) proceeded in the presence of a pyrene catalyst under light irradiation (λ = 365 nm) <a>to afford desired borylated products</a> and aminoborane as a byproduct. The yield of borylated product improved under a CO<sub>2</sub> atmosphere. Reactions conducted in the presence of a stoichiometric amount of aminoborane under N<sub>2</sub> or CO<sub>2</sub> indicated that CO<sub>2</sub> reduced the inhibitory effect of aminoborane. Optimal reaction conditions were applied to a variety of aromatic amines. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.

Metal-free visible-light-mediated organophotoredox catalysis: synthesis of 3-functionalized indole via C–C, C–N bond formation

2020 ◽  
Author(s):  
Neetu Yadav ◽  
Mohd Danish Ansari ◽  
Vijay B. Yadav ◽  
Ankit Verma ◽  
Saurabh K. Tiwari ◽  
...  
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Metal Free

scholarly journals Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 7051
Author(s):  
Lei Zhou
Keyword(s):  
Visible Light ◽  
Future Development ◽  
Bond Cleavage ◽  
Bond Formation ◽  
Environmentally Benign ◽  
Personal Perspective ◽  
Photoredox Catalysis ◽  
Recent Advances ◽  
The Future ◽  
The Creation

The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided.

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