Synthesis of trifluoromethylthioesters from aldehydes via a visible light-promoted radical process

2020 ◽  
Vol 18 (30) ◽  
pp. 5918-5926 ◽  
Author(s):  
Meng-Yue Wang ◽  
Xue-Qing Zhu ◽  
Xing-Long Zhang ◽  
Rui-Li Guo ◽  
Qiong Jia ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Process

An unprecedented visible light-promoted approach to the synthesis of trifluoromethylthioesters from aldehydes has been developed.

Visible-Light-Induced Nitrogen-Centered Radical Process for the Construction of 3-Acylcoumarins

2021 ◽  
Author(s):  
Quan Zhou ◽  
Fang-Ting Xiong ◽  
Pu Chen ◽  
Biquan Xiong ◽  
Kewen Tang ◽  
...  
Keyword(s):  
Visible Light ◽  
Cyclization Reactions ◽  
Radical Process

A nitrogen-centered radical-mediated strategy is described to synthesize functionalized 3-acylcoumarins. This process is enabled by visible-light-induced acylation/cyclization reactions of alkynoates with various acyl oxime compounds in acetonitrile. The difunctionalization of...

Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of C-Glycoamino Acids

2019 ◽  
Vol 21 (9) ◽  
pp. 3086-3092 ◽  
Author(s):  
Peng Ji ◽  
Yueteng Zhang ◽  
Yongyi Wei ◽  
He Huang ◽  
Wenbo Hu ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Process

Visible-light activated metal catalyst-free vicinal diazidation of olefins with sulfonium iodate(i) species

2019 ◽  
Vol 55 (19) ◽  
pp. 2833-2836 ◽  
Author(s):  
Thurpu Raghavender Reddy ◽  
Dodla Sivanageswara Rao ◽  
Sudhir Kashyap
Keyword(s):  
Visible Light ◽  
Late Stage ◽  
Metal Catalyst ◽  
Radical Process ◽  
Biologically Relevant ◽  
Catalyst Free

An unprecedented visible-light inspired selective radical azidation of unactivated and diverse substituted vinylarenes with sulfonium iodate reagent has been realized. The intrinsic radical process triggered by light tolerated several synthetically useful functionalities enabling two new carbon-hetero bonds which display distinctive late-stage applications to biologically relevant scaffolds.

scholarly journals A visible-light mediated three-component radical process using dithiocarbamate anion catalysis

2019 ◽  
Vol 10 (21) ◽  
pp. 5484-5488 ◽  
Author(s):  
Sara Cuadros ◽  
Matthew A. Horwitz ◽  
Bertrand Schweitzer-Chaput ◽  
Paolo Melchiorre
Keyword(s):  
Visible Light ◽  
Catalytic Mechanism ◽  
Radical Process ◽  
Biologically Relevant

A three-component radical process is reported that, by coupling alkyl chlorides, maleimides, and heteroaromatic fragments, installs multiple biologically relevant heterocycles within complex cascade products. This method, which generates radicals via an SN2-based photochemical catalytic mechanism, activates substrates incompatible with or inert to classical radical-generating strategies.

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...

Thiourea dioxide as a source of sulfonyl groups: photoredox generation of sulfones and sulfonamides from heteroaryl/aryl halides

2019 ◽  
Vol 55 (17) ◽  
pp. 2489-2492 ◽  
Author(s):  
Shengqing Ye ◽  
Yuewen Li ◽  
Jie Wu ◽  
Zhiming Li
Keyword(s):  
Dft Calculations ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Epr Spectroscopy ◽  
Aryl Halides ◽  
Light Irradiation ◽  
Efficient Synthesis ◽  
Radical Process ◽  
Thiourea Dioxide

Thiourea dioxide is applied as the source of sulfonyl groups for the efficient synthesis of heteroaryl sulfones and sulfonamides from heteroaryl halides under visible light irradiation. This transformation proceeds through a radical process via heteroaryl sulfinate intermediates, as supported by EPR spectroscopy and DFT calculations.

scholarly journals Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

2021 ◽  
Vol 17 ◽  
pp. 551-557
Author(s):  
Xiaojuan Li ◽  
Qiang Zhang ◽  
Weigang Zhang ◽  
Jinzhu Ma ◽  
Yi Wang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Complex Molecules ◽  
Radical Process ◽  
Metal Free ◽  
Mild Conditions

The difunctionalization of alkenes involving a trifluoromethylthio group (SCF3) for the conversion of versatile and readily available olefins into structurally more complex molecules has been successfully studied. However, the disproportionate dithiolation of alkenes is unknown. Herein, a transition-metal-free protocol is presented for the vicinal trifluoromethylthio–thiolation of unactivated alkenes via a radical process under mild conditions with a broad substrate scope and excellent tolerance.

Visible-Light Photoredox-catalyzed Decarboxylative α-tertiary butylation of C(sp3)−H Bond of N-aryl tetrahydroisoquinolines with Pivalic acid under Transition-metal-free Conditions

Synlett ◽  
2021 ◽  
Author(s):  
Li Sun ◽  
Yicheng Zhang ◽  
jie liu ◽  
Pinhua Li
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Groups ◽  
Pivalic Acid ◽  
Mechanistic Study ◽  
Radical Process ◽  
Metal Free

A transition-metal-free visible-light photoredox-catalyzed decarboxylative alkylation of benzylic C-(sp3)−H bonds of N-aryl tetrahydroisoquinolines is reported. The developed methodology tolerates various functional groups and proceeds smoothly without the requirement of stoichiometric oxidants. A preliminary mechanistic study indicated that a radical process is involved in the reaction.

scholarly journals Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

2021 ◽  
Author(s):  
Xiaojuan Li ◽  
Qiang Zhang ◽  
Weigang Zhang ◽  
Jinzhu Ma ◽  
Yi Wang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Mild Condition ◽  
Complex Molecules ◽  
Radical Process ◽  
Metal Free

The difunctionalization of alkenes involving trifluoromethylthio group (SCF3) for the conversion of versatile and readily available olefins into more structurally complex molecules has been greatly studied. However, the disproportionate dithiolation of alkene is unknown. Herein, a transition-metal-free protocol is presented for vicinal trifluoromethylthio-thiolation of unactivated alkenes via a radical process under mild condition with broad substrate scope and excellent tolerance.

Visible-Light-Driven Oxidation of N-Alkylamides to Imides Using Oxone/H2O and Catalytic KBr

Synthesis ◽  
2018 ◽  
Vol 50 (15) ◽  
pp. 2999-3005 ◽  
Author(s):  
Wenjun Lu ◽  
Chong Mei ◽  
Yixin Hu
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Experimental Studies ◽  
Catalytic Amount ◽  
White Led ◽  
Radical Process ◽  
Mild Conditions ◽  
Visible Light Driven

Imides are prepared conveniently by visible-light-driven oxidations of various N-alkylamides under mild conditions. The majority of the reactions proceed efficiently by using Oxone as the oxidant in the presence of a catalytic amount of KBr in H2O/CH2Cl2 under irradiation by an 8 W white LED at room temperature. Experimental studies suggest that an imine, obtained from the substrate amide via a radical process, is the key intermediate.

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