Mechanistic studies on propargyl alcohol‐tethered alkylidenecyclopropane with aryldiazonium salt initiated by visible light

Author(s):  
Jiaxin Liu ◽  
Yin Wei ◽  
Min Shi
2017 ◽  
Vol 56 (48) ◽  
pp. 15309-15313 ◽  
Author(s):  
Philippe Nuhant ◽  
Martins S. Oderinde ◽  
Julien Genovino ◽  
Antoine Juneau ◽  
Yohann Gagné ◽  
...  

Synlett ◽  
2017 ◽  
Vol 28 (13) ◽  
pp. 1558-1563 ◽  
Author(s):  
Aiwen Lei ◽  
Atul Singh ◽  
Hong Yi ◽  
Guoting Zhang ◽  
Changliang Bian ◽  
...  

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.


Synlett ◽  
2020 ◽  
Vol 31 (14) ◽  
pp. 1372-1377
Author(s):  
Shinji Harada ◽  
Daiki Matsuda ◽  
Takahiro Morikawa ◽  
Atsushi Nishida

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.


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

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 219-226 ◽  
Author(s):  
Ce Liang ◽  
Wang-Tao Zhuo ◽  
Yan-Ning Niu ◽  
Guo-Lin Gao

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.


Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  

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.


2016 ◽  
Vol 14 (29) ◽  
pp. 7028-7037 ◽  
Author(s):  
Xiao-Fei Wang ◽  
Shu-Sheng Yu ◽  
Chao Wang ◽  
Dong Xue ◽  
Jianliang Xiao

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.


2021 ◽  
Author(s):  
Xiao-Yu Zhang ◽  
Chao Ning ◽  
Ben Mao ◽  
Yin Wei ◽  
Min Shi

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...


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