Regio- and stereoselective C(sp2)–H acylation of enamides with aldehydes via transition-metal-free photoredox catalysis

2020 ◽  
Vol 22 (16) ◽  
pp. 5497-5503 ◽  
Author(s):  
Kai Zhao ◽  
Xiao-Chen Zhang ◽  
Ji-Yu Tao ◽  
Xian-Dan Wu ◽  
Jia-Xu Wu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Environmentally Friendly ◽  
Photoredox Catalysis ◽  
Metal Free

A regio- and stereoselective β-C(sp2)–H acylation of enamides with aldehydes is demonstrated, affording geometrically defined acylated enamides under environmentally friendly conditions.

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.

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.

Understanding the Kinetics and Spectroscopy of Photoredox Catalysis and Transition-Metal-Free Alternatives

2016 ◽  
Vol 49 (6) ◽  
pp. 1320-1330 ◽  
Author(s):  
Spencer P. Pitre ◽  
Christopher D. McTiernan ◽  
Juan C. Scaiano
Keyword(s):  
Transition Metal ◽  
Photoredox Catalysis ◽  
Metal Free

Synthesis of oxindoles through trifluoromethylation of N-aryl acrylamides by photoredox catalysis

2018 ◽  
Vol 16 (35) ◽  
pp. 6564-6568 ◽  
Author(s):  
Maojian Lu ◽  
Zhiji Liu ◽  
Jinwang Zhang ◽  
Yu Tian ◽  
Honggui Qin ◽  
...  
Keyword(s):  
Transition Metal ◽  
Photoredox Catalysis ◽  
Metal Free

A photocatalytic trifluoromethylation of activated alkenes has been established to access CF3-containing oxindoles under strong oxidant and transition metal free conditions.

Transition-Metal-Free Synthesis of Pyridine Derivatives by Thermal Cyclization of N-Propargyl Enamines

Synthesis ◽  
2020 ◽  
Vol 52 (07) ◽  
pp. 1113-1121 ◽  
Author(s):  
Yuya Chikayuki ◽  
Takakane Miyashige ◽  
Shiori Yonekawa ◽  
Akiko Kirita ◽  
Natsuko Matsuo ◽  
...  
Keyword(s):  
Transition Metal ◽  
Total Synthesis ◽  
Good Yield ◽  
Environmentally Friendly ◽  
Thermal Cyclization ◽  
Pyridine Derivatives ◽  
Atom Economy ◽  
Metal Free

A transition-metal-free synthesis of pyridine derivatives by 6-endo-dig cyclization of N-propargyl enamines was developed. This method is environmentally friendly and is a high atom economy reaction that is easily accessed to provide pyridine derivatives in moderate to good yield by heating N-propargyl enamines in solvent without additives. The total synthesis of onychine was achieved in 51% yield in only two steps by using this method.

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

2019 ◽  
Vol 84 (12) ◽  
pp. 7796-7803 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Ashok Polu ◽  
Nagaraj Sabarinathan ◽  
Manickam Bakthadoss ◽  
...  
Keyword(s):  
Transition Metal ◽  
Photoredox Catalysis ◽  
Metal Free

scholarly journals Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts

2021 ◽  
Vol 14 (7) ◽  
pp. 661
Author(s):  
Thierry Besson ◽  
Corinne Fruit
Keyword(s):  
Transition Metal ◽  
Late Stage ◽  
Heterocyclic Compounds ◽  
Environmentally Friendly ◽  
Direct Arylation ◽  
Stepping Stone ◽  
Metal Free ◽  
Bond Forming ◽  
Diaryliodonium Salts ◽  
Recent Advances

Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

scholarly journals Solvent- and transition metal-free amide synthesis from phenyl esters and aryl amines

RSC Advances ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 1536-1540 ◽  
Author(s):  
Sergey A. Rzhevskiy ◽  
Alexandra A. Ageshina ◽  
Gleb A. Chesnokov ◽  
Pavel S. Gribanov ◽  
Maxim A. Topchiy ◽  
...  
Keyword(s):  
Transition Metal ◽  
Environmentally Friendly ◽  
Solvent Free ◽  
Metal Free ◽  
Amide Synthesis ◽  
Aryl Amines ◽  
Environmentally Friendly Approach

A new environmentally friendly approach to transition metal- and solvent-free amide synthesis from aryl esters and aryl amines is described.

Transition Metal-Free Supramolecular Photoredox Catalysis in Water: A Phenoxazine Photocatalyst Encapsulated in V-Shaped Aromatic Amphiphiles

ACS Catalysis ◽  
2020 ◽  
Vol 10 (23) ◽  
pp. 14283-14289
Author(s):  
Naoki Noto ◽  
Yuki Hyodo ◽  
Michito Yoshizawa ◽  
Takashi Koike ◽  
Munetaka Akita
Keyword(s):  
Transition Metal ◽  
Photoredox Catalysis ◽  
Metal Free
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