Visible-Light-Initiated Manganese Catalysis for C−H Alkylation of Heteroarenes: Applications and Mechanistic Studies

2017 ◽  
Vol 56 (48) ◽  
pp. 15309-15313 ◽  
Author(s):  
Philippe Nuhant ◽  
Martins S. Oderinde ◽  
Julien Genovino ◽  
Antoine Juneau ◽  
Yohann Gagné ◽  
...  
Keyword(s):  
Visible Light ◽  
Mechanistic Studies

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.

Direct Synthesis of Enones by Visible-Light-Promoted Oxygenation of Trisubstituted Olefins Using Molecular Oxygen

Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1372-1377
Author(s):  
Shinji Harada ◽  
Daiki Matsuda ◽  
Takahiro Morikawa ◽  
Atsushi Nishida
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Active Oxygen Species ◽  
Direct Synthesis ◽  
Reaction System ◽  
Active Oxygen ◽  
Oxygen Species ◽  
Mechanistic Studies ◽  
Trisubstituted Olefins ◽  
One Step

A one-step synthesis of enones from olefins is described. The reaction was performed under visible-light irradiation in the presence of molecular oxygen and a photocatalyst. The reaction proceeded with various types of trisubstituted olefins to give enones in good yields with high regioselectivity. In particular, oxygen- and nitrogen-containing functional groups, heteroaromatic rings, and cyclopropanes were tolerated. Mechanistic studies and previous reports indicated that the active oxygen species generated in the reaction system is singlet oxygen.

Visible-Light-Initiated Manganese Catalysis for C−H Alkylation of Heteroarenes: Applications and Mechanistic Studies

2017 ◽  
Vol 129 (48) ◽  
pp. 15511-15515 ◽  
Author(s):  
Philippe Nuhant ◽  
Martins S. Oderinde ◽  
Julien Genovino ◽  
Antoine Juneau ◽  
Yohann Gagné ◽  
...  
Keyword(s):  
Visible Light ◽  
Mechanistic Studies

Visible-Light-Promoted C2 Trifluoromethylation of Quinoline N-Oxides

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 219-226 ◽  
Author(s):  
Ce Liang ◽  
Wang-Tao Zhuo ◽  
Yan-Ning Niu ◽  
Guo-Lin Gao
Keyword(s):  
Visible Light ◽  
Functional Groups ◽  
Room Temperature ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Reaction Proceeds

A photoredox catalytic strategy has been described for the direct C2 trifluoromethylation of quinoline N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2 trifluoromethyl quinoline N-oxides at room temperature. Mechanistic studies indicated that the reaction proceeds via a radical pathway.

Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Regioselective Alkylation ◽  
Decarboxylative Coupling ◽  
Aliphatic Carboxylic Acids

A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

BODIPY catalyzed amide synthesis promoted by BHT and air under visible light

2016 ◽  
Vol 14 (29) ◽  
pp. 7028-7037 ◽  
Author(s):  
Xiao-Fei Wang ◽  
Shu-Sheng Yu ◽  
Chao Wang ◽  
Dong Xue ◽  
Jianliang Xiao
Keyword(s):  
Visible Light ◽  
Aromatic Aldehydes ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Amide Synthesis ◽  
Oxidative Amidation

A novel and efficient protocol for the synthesis of amides is reported via a BODIPY catalyzed oxidative amidation of aromatic aldehydes under visible light, with broad substrate scope and mild reaction conditions. Mechanistic studies reveal that dioxygen could be activated through both an ET and SET pathway to form the active peroxide intermediates.

scholarly journals Visible-light Mediated Ring Opening Reaction of Alkylidenecyclopropanes for the Generation of Homopropargyl Radical

2021 ◽  
Author(s):  
Xiao-Yu Zhang ◽  
Chao Ning ◽  
Ben Mao ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Molecular Structure ◽  
Visible Light ◽  
Ring Opening ◽  
Mechanistic Studies ◽  
Radical Process ◽  
Ring Opening Reaction ◽  
Long Time ◽  
Radical Clock

Classical cyclopropylcarbinyl radical clock reactions have been widely applied to conduct the mechanistic studies on probing radical process for a long time; however, alkylidenecyclopropanes, which have a similar molecular structure...

scholarly journals Visible-Light Photoredox-Catalyzed C–O Bond Cleavage of Diaryl Ethers by Acridinium Photocatalysts at Room Temperature

2020 ◽  
Author(s):  
Fang-Fang Tan ◽  
Xiao-Ya He He ◽  
Wan-Fa Tian ◽  
Yang Li
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Acid Catalysis ◽  
Bond Cleavage ◽  
Diphenyl Ether ◽  
Mechanistic Studies ◽  
Electrophilic Attack ◽  
One Pot ◽  
Diaryl Ethers ◽  
Diaryl Ether

Abstract We have developed visible-light photoredox-catalyzed C–O bond cleavage of diaryl ethers by an acidolysis with an aryl car-boxylic acid and a following one-pot hydrolysis. Two phenols are obtained from a diaryl ether at room temperature. The aryl carboxylic acid used for the acidolysis can be recovered. The key to success of the acidolysis is merging visible-light photore-dox catalysis with a new acridinium photocatalyst and Lewic acid catalysis with Cu(TMHD)2. Preliminary mechanistic studies indicate that the catalytic cycle occurs via a rare selective electrophilic attack of the generated aryl carboxylic radical on the electron-rich aryl ring of diphenyl ether. This transformation is applied to a gram-scale reaction and the model of 4-O-5 lignin linkages.

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