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 ◽  
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.

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.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Highly chemoselective deoxygenation of N-heterocyclic N-oxides under transition metal-free conditions

2021 ◽  
Vol 19 (16) ◽  
pp. 3735-3742
Author(s):  
Se Hyun Kim ◽  
Ju Hyeon An ◽  
Jun Hee Lee
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Eosin Y ◽  
Metal Free ◽  
Simple Protocol

Here, we provide an operationally simple protocol for the highly chemoselective deoxygenation of various functionalized N-heterocyclic N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst.

scholarly journals Mechanistic Study on the Reaction of pinB-BMes2 with Alkynes Based on Experimental Investigation and DFT Calculations: Gradual Change of Mechanism Depending on the Substituent

2021 ◽  
Author(s):  
Linlin Wu ◽  
Chiemi Kojima ◽  
Ka Ho Lee ◽  
Shogo Morisako ◽  
Zhenyang Lin ◽  
...  
Keyword(s):  
Experimental Investigation ◽  
Transition Metal ◽  
Dft Calculations ◽  
Kinetic Analysis ◽  
Reaction Rate ◽  
Mechanistic Study ◽  
Isomer Ratio ◽  
Gradual Change ◽  
Isomeric Mixture ◽  
Metal Free

Transition-metal free direct and base-catalyzed 1,2-diborations of arylacetylenes using pinB-BMes2 provided syn/anti-isomeric mixture of diborylalkenes. The kinetic analysis showed that the reaction rate and isomer ratio were affected by reaction...

Deuterative cyclization of sulfanyl 1,6-diynes: complete and monodeuteration of functional groups on heterocycles

2015 ◽  
Vol 2 (3) ◽  
pp. 201-205 ◽  
Author(s):  
Yukiteru Ito ◽  
Mitsuhiro Yoshimatsu
Keyword(s):  
Transition Metal ◽  
Exchange Reaction ◽  
Functional Groups ◽  
Reductive Cyclization ◽  
Metal Free ◽  
Sodium Borodeuteride

Regioselective H/D exchange reaction of functional groups on heterocycles proceeded via a transition metal-free reductive cyclization of sulfanyl 1,6-diynes using sodium borodeuteride/ethanol-D1.

New Avenues in Radical Trifluoromethylselenylation with ­Trifluoromethyl Tolueneselenosulfonate

Synlett ◽  
2018 ◽  
Vol 30 (07) ◽  
pp. 777-782 ◽  
Author(s):  
Clément Ghiazza ◽  
Cyrille Monnereau ◽  
Lhoussain Khrouz ◽  
Maurice Médebielle ◽  
Thierry Billard ◽  
...  
Keyword(s):  
Cyclic Voltammetry ◽  
Transition Metal ◽  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Diazonium Salts ◽  
Metal Free ◽  
Luminescence Measurement ◽  
Stable Reagent ◽  
Shelf Stable

We demonstrated that the shelf-stable reagent trifluoromethyl tolueneselenosulfonate can be involved in radical trifluoromethylselenylation. Upon visible-light irradiation, the homolysis of the reagent could take place at room temperature. This finding is explored for unprecedented C(sp2)–SeCF3 and C(sp3)–SeCF3 processes under transition-metal-free conditions. Mechanistic investigations, including cyclic voltammetry, luminescence measurement, and EPR studies, allowed the proposal of plausible mechanisms.1 Introduction.2 Reactivity of Reagent I with Diazonium Salts3 Reactivity of Reagent I with Alkenes and Alkynes4 Conclusion

scholarly journals Photocatalytic Synthesis of Tetra-Substituted Furans Promoted by Carbon Dioxide

2021 ◽  
Author(s):  
Ya-Ming Tian ◽  
Huaiju Wang ◽  
Ritu Ritu ◽  
Burkhard Koenig
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Visible Light ◽  
Metal Free ◽  
Mild Conditions ◽  
Simple Protocol ◽  
Visible Light Driven ◽  
Substituted Furans ◽  
Photocatalytic Synthesis

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that...

Visible light-mediated transition metal-free esterification of amides with boronic acids

2020 ◽  
Vol 61 (43) ◽  
pp. 152444
Author(s):  
Hao Ding ◽  
Wan-Ying Qi ◽  
Jing-Song Zhen ◽  
Qiuping Ding ◽  
Yong Luo
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Boronic Acids ◽  
Metal Free

Metal-free photocatalytic trifluoromethylative pyridylation of unactivated alkenes

2018 ◽  
Vol 20 (22) ◽  
pp. 5209-5214 ◽  
Author(s):  
Yu-Tao He ◽  
Dahye Kang ◽  
Inwon Kim ◽  
Sungwoo Hong
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Photoredox Catalysis ◽  
Metal Free

An efficient, transition metal-free trifluoromethylative pyridylation of unactivated alkenes was achieved by visible-light-induced photoredox catalysis.

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