A Visible Light Photoredox Catalysed Radical Pictet-Spengler Reaction

2020 ◽  
Vol 73 (3) ◽  
pp. 189
Author(s):  
Theerada Seehamongkol ◽  
Tyra H. Horngren ◽  
Mohammed A. M. Alhajji ◽  
Joshua Almond-Thynne ◽  
Milena L. Czyz ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Photoredox Catalysis ◽  
Thermal Transformations ◽  
Complementary Method ◽  
Reaction Proceeds ◽  
Radical Approach

A methodology for a radical Pictet–Spengler reaction promoted by visible light photoredox catalysis is described. This strategy furnishes tetrahydroisoquinoline derivatives bearing electron poor and electron rich substituents. The reaction proceeds at room temperature and with excellent regioselectivity for the 6-endo intramolecular cyclisation. This radical approach provides a complementary method for the synthesis of the tetrahydroisoquinoline scaffold with substitution patterns inaccessible via established thermal transformations.

scholarly journals Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

2018 ◽  
Vol 14 ◽  
pp. 2520-2528 ◽  
Author(s):  
Amrita Das ◽  
Mitasree Maity ◽  
Simon Malcherek ◽  
Burkhard König ◽  
Julia Rehbein
Keyword(s):  
Visible Light ◽  
Experimental Evidence ◽  
Blue Light ◽  
Room Temperature ◽  
Cross Coupling ◽  
Light Irradiation ◽  
Coupling Mechanism ◽  
Photoredox Catalysis ◽  
Reaction Proceeds ◽  
Aryl Sulfides

Electron-rich arenes react with aryl and alkyl disulfides in the presence of catalytic amounts of [Ir(dF(CF3)ppy)2(dtbpy)]PF6 and (NH4)2S2O8 under blue light irradiation to yield arylthiols. The reaction proceeds at room temperature and avoids the use of prefunctionalized arenes. Experimental evidence suggests a radical–radical cross coupling mechanism.

Phthalide synthesis through dehydrogenated lactonization of the C(sp3)–H bond by photoredox catalysis

2021 ◽  
Author(s):  
Hui Liu ◽  
Chao Liu ◽  
Shanyi Chen ◽  
Qihong Lai ◽  
Yulin Lin ◽  
...  
Keyword(s):  
Visible Light ◽  
Efficient Method ◽  
Room Temperature ◽  
Photoredox Catalysis ◽  
Metal Free

An efficient method for the direct oxidative lactonization of the C(sp3)–H bonds of benzyl via visible-light-induced photoredox catalysis. The metal-free protocol delivers diverse phthalides using O2 as the sole terminal oxidant at room temperature.

ChemInform Abstract: Room Temperature C-P Bond Formation Enabled by Merging Nickel Catalysis and Visible-Light-Induced Photoredox Catalysis.

ChemInform ◽  
2015 ◽  
Vol 46 (32) ◽  
pp. no-no
Author(s):  
Jun Xuan ◽  
Ting-Ting Zeng ◽  
Jia-Rong Chen ◽  
Liang-Qiu Lu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Nickel Catalysis ◽  
Photoredox Catalysis

PQS-enabled visible-light iridium photoredox catalysis in water at room temperature

2018 ◽  
Vol 20 (6) ◽  
pp. 1233-1237 ◽  
Author(s):  
Mei-jie Bu ◽  
Chun Cai ◽  
Fabrice Gallou ◽  
Bruce H. Lipshutz
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Photoredox Catalysis

A new photocatalyst attached to the designer surfactant PQS has been developed that self-aggregates into micelles, thereby enabling photoredox catalysis conducted in water at room temperature without any additives or co-solvents.

ChemInform Abstract: Metal-Free, Room-Temperature, Radical Alkoxycarbonylation of Aryldiazonium Salts Through Visible-Light Photoredox Catalysis.

ChemInform ◽  
2015 ◽  
Vol 46 (25) ◽  
pp. no-no
Author(s):  
Wei Guo ◽  
Liang-Qiu Lu ◽  
Yue Wang ◽  
Ya-Ni Wang ◽  
Jia-Rong Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Photoredox Catalysis ◽  
Metal Free

Metal-Free, Room-Temperature, Radical Alkoxycarbonylation of Aryldiazonium Salts through Visible-Light Photoredox Catalysis

2014 ◽  
Vol 54 (7) ◽  
pp. 2265-2269 ◽  
Author(s):  
Wei Guo ◽  
Liang-Qiu Lu ◽  
Yue Wang ◽  
Ya-Ni Wang ◽  
Jia-Rong Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Photoredox Catalysis ◽  
Metal Free

Room Temperature CP Bond Formation Enabled by Merging Nickel Catalysis and Visible-Light-Induced Photoredox Catalysis

2015 ◽  
Vol 21 (13) ◽  
pp. 4962-4965 ◽  
Author(s):  
Jun Xuan ◽  
Ting-Ting Zeng ◽  
Jia-Rong Chen ◽  
Liang-Qiu Lu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Bond Formation ◽  
Nickel Catalysis ◽  
Photoredox Catalysis

Aliphatic Radical Relay Heck Reaction at Unactivated C(sp3)–H Sites of Alcohols

2018 ◽  
Author(s):  
Padon Chuentragool ◽  
Dongari Yadagiri ◽  
Taiki Morita ◽  
Sumon Sarkar ◽  
Marvin Parasram ◽  
...  
Keyword(s):  
Visible Light ◽  
Heck Reaction ◽  
Room Temperature ◽  
Halogen Atom ◽  
Organic Molecules ◽  
Alkyl Halides ◽  
Aliphatic Alcohols ◽  
Aliphatic Radical ◽  
Reaction Proceeds

<div>The Mizoroki−Heck reaction is one of the most efficient methods for alkenylation of</div><div>aryl, vinyl, and alkyl halides. Due to its innate nature, this protocol requires the employment of compounds possessing a halogen atom at the site of functionalization. However, the accessibility of organic molecules possessing a halogen atom at a particular site in aliphatic systems is extremely limited. Thus, a protocol that would allow a Heck reaction to occur at a specific non-functionalized C(sp3)−H site would be highly desirable.</div><div>Here, we report a radical relay Heck reaction which allows for a selective remote</div>alkenylation of aliphatic alcohols at unactivated β-, γ- and δ-C(sp3 20 )–H sites. The use of easily installable/removable Si-based auxiliary enables selective I-atom/radical translocation events at remote C−H sites followed by the Heck reaction. Notably, the reaction proceeds smoothly under mild visible light-mediated conditions at room temperature, producing highly modifiable and valuable alkenol products from readily available alcohols feedstocks. <br>

Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis

2014 ◽  
Vol 50 (18) ◽  
pp. 2308-2310 ◽  
Author(s):  
Pan Xu ◽  
Ablimit Abdukader ◽  
Kaidong Hu ◽  
Yixiang Cheng ◽  
Chengjian Zhu
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Photoredox Catalysis ◽  
Unsaturated Carboxylic Acids

A visible-light-induced decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed.

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.

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