Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
Author(s):  
Can Jin ◽  
Bin Sun ◽  
Tengwei Xu ◽  
Liang Zhang ◽  
Rui Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Mechanistic Studies ◽  
Metal Free ◽  
Regioselective Alkylation ◽  
Decarboxylative Coupling ◽  
Aliphatic Carboxylic Acids

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.

Transition-metal-free visible-light photoredox catalysis at room-temperature for decarboxylative fluorination of aliphatic carboxylic acids by organic dyes

2015 ◽  
Vol 51 (59) ◽  
pp. 11864-11867 ◽  
Author(s):  
Xinxin Wu ◽  
Chunna Meng ◽  
Xiaoqian Yuan ◽  
Xiaotong Jia ◽  
Xuhong Qian ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Organic Dyes ◽  
Photoredox Catalysis ◽  
Green Method ◽  
Metal Free ◽  
Aliphatic Carboxylic Acids

We report herein an efficient, general and green method for decarboxylative fluorination of aliphatic carboxylicacids.

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.

Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

2019 ◽  
Vol 6 (13) ◽  
pp. 2245-2249 ◽  
Author(s):  
Guibing Wu ◽  
Jingwen Wang ◽  
Chengyu Liu ◽  
Maolin Sun ◽  
Lei Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Radical Addition ◽  
Metal Free ◽  
Radical Coupling

A metal-free photoredox catalyzed decarboxylative radical coupling of free-carboxylic acids and glyoxylic oximes was developed to synthesize α,β-diamino acids.

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 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.

Synthesis of 6-Thiocyanatophenanthridines by Visible-Light- and Air-Promoted Radical Thiocyanation of 2-Isocyanobiphenyls

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 176-180 ◽  
Author(s):  
Manjula Singh ◽  
Arvind Yadav ◽  
Lal Yadav ◽  
R. Singh
Keyword(s):  
Natural Resources ◽  
Visible Light ◽  
Room Temperature ◽  
Atmospheric Oxygen ◽  
Ammonium Thiocyanate ◽  
Radical Cyclization ◽  
Eosin Y ◽  
One Pot ◽  
Metal Free

A convenient, efficient, and metal-free synthesis of 6-thiocyanatophenanthridines by visible-light- and air-mediated, eosin Y-catalyzed, sequential radical cyclization and aromatization of 2-isocyanobiphenyls with ammonium thiocyanate is reported. Advantageously, the protocol utilizes inexpensive, clean, and sustainable natural resources such as visible light and atmospheric oxygen at room temperature in a one-pot procedure.

Retracted Article: Visible-light-induced oxidative difunctionalization of styrenes: synthesis of α-trifluoromethylthio-substituted ketones

2018 ◽  
Vol 54 (16) ◽  
pp. 1976-1979 ◽  
Author(s):  
Arvind Kumar Yadav ◽  
Krishna Nand Singh
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Present Approach ◽  
Eosin Y ◽  
Photoredox Catalysis ◽  
Retracted Article ◽  
Oxidative Difunctionalization

Synthesis of α-trifluoromethylthio-substituted ketones has been accomplished through photoredox catalysis from easily accessible styrenes. The present approach involves the use of inexpensive eosin Y as an organophotoredox catalyst and a CF3SO2Na/CS2 blend as a new source of SCF3 radicals at room temperature.

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

2015 ◽  
Vol 127 (7) ◽  
pp. 2293-2297 ◽  
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
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