scholarly journals Room temperature Palladium-Catalyzed C─H Functionalization of Benzothiazole with Iodo(Hetero)Arenes

2020 ◽  
Author(s):  
Yuvraj Bhujbal ◽  
kamlesh vadagaonkar ◽  
santosh kori ◽  
Anant Kapdi
Keyword(s):  
Room Temperature ◽  
Antitumor Agent ◽  
One Pot ◽  
Direct Arylation ◽  
Palladium Catalyzed

A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodo(hetero)arenes under palladium-catalyzed conditions and promoted by HFIP as the reaction solvent has been presented herewith. An in-situ one-pot sequential HFIP promoted selective iodination of (hetero)arenes followed by Pd-catalyzed direct arylation of benzothiazole has also been disclosed. Synthesis of PMX 610 (antitumor agent) analog has been disclosed and also CJM 126 (antitumor agent) has been synthesized.

scholarly journals Room temperature Palladium-Catalyzed C─H Functionalization of Benzothiazole with Iodo(Hetero)Arenes

2020 ◽  
Author(s):  
Yuvraj Bhujbal ◽  
kamlesh vadagaonkar ◽  
santosh kori ◽  
Anant Kapdi
Keyword(s):  
Room Temperature ◽  
Antitumor Agent ◽  
One Pot ◽  
Direct Arylation ◽  
Palladium Catalyzed

A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodo(hetero)arenes under palladium-catalyzed conditions and promoted by HFIP as the reaction solvent has been presented herewith. An in-situ one-pot sequential HFIP promoted selective iodination of (hetero)arenes followed by Pd-catalyzed direct arylation of benzothiazole has also been disclosed. Synthesis of PMX 610 (antitumor agent) analog has been disclosed and also CJM 126 (antitumor agent) has been synthesized.

Palladium-Catalyzed One-Pot Synthesis of C2-Quaternary Indolin-3-ones via 1H -indole-3-sulfonates Generated in Situ from 2-Alkynyl Arylazides and Sulfonic Acids

2017 ◽  
Vol 359 (23) ◽  
pp. 4147-4152 ◽  
Author(s):  
Xiaoxiang Zhang ◽  
Ping Li ◽  
Chang Lyu ◽  
Wanxiong Yong ◽  
Jing Li ◽  
...  
Keyword(s):  
Sulfonic Acids ◽  
One Pot ◽  
One Pot Synthesis ◽  
Palladium Catalyzed

Facile synthesis of chiral indolines through asymmetric hydrogenation of in situ generated indoles

2018 ◽  
Vol 5 (19) ◽  
pp. 2805-2809 ◽  
Author(s):  
Chang-Bin Yu ◽  
Jie Wang ◽  
Yong-Gui Zhou
Keyword(s):  
Asymmetric Hydrogenation ◽  
Hydrogenation Process ◽  
Bronsted Acid ◽  
Brønsted Acid ◽  
Facile Synthesis ◽  
One Pot ◽  
Brönsted Acid ◽  
Palladium Catalyzed ◽  
Intramolecular Condensation

A concise synthesis of chiral indolines has been developed through intramolecular condensation, deprotection and palladium-catalyzed asymmetric hydrogenation in a one-pot process with up to 96% ee. A strong Brønsted acid played an important role in both the formation of indoles and asymmetric hydrogenation process.

Palladium-Catalyzed One-Pot Stereospecific Synthesis of 2-Deoxy Aryl C-Glycosides from Glycals and Anilines in the Presence of tert-Butyl Nitrite

Synthesis ◽  
2019 ◽  
Vol 51 (22) ◽  
pp. 4215-4230 ◽  
Author(s):  
Adesh Kumar Singh ◽  
Rapelly Venkatesh ◽  
Jeyakumar Kandasamy
Keyword(s):  
Room Temperature ◽  
Stereospecific Synthesis ◽  
One Pot ◽  
Tert Butyl ◽  
Mild Conditions ◽  
One Pot Synthesis ◽  
Palladium Catalyzed ◽  
Aryl Glycosides

The palladium-catalyzed one-pot synthesis of 2,3-deoxy-3-keto aryl C-glycosides is achieved from glycals and anilines in the presence of tert-butyl nitrite and aqueous HBF4 under mild conditions. This one-pot method stereospecifically provides α- and β-aryl glycosides (≥19:1 by NMR) in good yields at room temperature. The configuration at the C-3 position in the glycal determines the anomeric selectivity (i.e., α or β) of the desired products.

scholarly journals Difunctionalization of alkenes with iodine and tert-butyl hydroperoxide (TBHP) at room temperature for the synthesis of 1-(tert-butylperoxy)-2-iodoethanes

2017 ◽  
Vol 13 ◽  
pp. 2023-2027 ◽  
Author(s):  
Hao Wang ◽  
Cui Chen ◽  
Weibing Liu ◽  
Zhibo Zhu
Keyword(s):  
Room Temperature ◽  
Synthetic Methods ◽  
Chemical Modifications ◽  
One Pot ◽  
Butyl Hydroperoxide ◽  
Radical Intermediates ◽  
Mild Conditions ◽  
Tert Butyl Hydroperoxide ◽  
Potential Applications

We developed a direct vicinal difunctionalization of alkenes with iodine and TBHP at room temperature. This iodination and peroxidation in a one-pot synthesis produces 1-(tert-butylperoxy)-2-iodoethanes, which are inaccessible through conventional synthetic methods. This method generates multiple radical intermediates in situ and has excellent regioselectivity, a broad substrate scope and mild conditions. The iodine and peroxide groups of 1-(tert-butylperoxy)-2-iodoethanes have several potential applications and allow further chemical modifications, enabling the preparation of synthetically valuable molecules.

Palladium-catalyzed one-pot cycloaddition reactions of thioureas with 3H-indol-3-ones generated in situ from 2-alkynyl arylazides: rapid and efficient access to imidazoloindolines

2020 ◽  
Vol 7 (21) ◽  
pp. 3480-3485
Author(s):  
Ping Li ◽  
Boyu Zhu ◽  
Yao Xu ◽  
Zhiqiang Zhou ◽  
Guiwen Hu ◽  
...  
Keyword(s):  
Cycloaddition Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Efficient Access ◽  
Palladium Catalyzed

An efficient palladium-catalyzed one-pot synthesis of imidazoloindolines from 2-alkynyl arylazides under mild reaction conditions has been described.

Room-Temperature One-Pot Palladium-Catalyzed Synthesis of 3-Hydroxyisoindolin-1-ones from Phenylglyoxylic Acids

Heterocycles ◽  
2016 ◽  
Vol 92 (3) ◽  
pp. 560 ◽  
Author(s):  
Na Li ◽  
Menglei Yuan ◽  
Yu Sun ◽  
Hui Yan ◽  
Jinxiong Wu ◽  
...  
Keyword(s):  
Room Temperature ◽  
One Pot ◽  
Palladium Catalyzed

scholarly journals One-Pot Synthesis of (Z)-β-Halovinyl Ketones via the Cascade of Sonogashira Coupling and Hydrohalogenation

2021 ◽  
Vol 8 ◽  
Author(s):  
Fa-Jie Chen ◽  
Zhenguo Hua ◽  
Jianhui Chen ◽  
Jiajia Chen ◽  
Daesung Lee ◽  
...  
Keyword(s):  
Efficient Method ◽  
Room Temperature ◽  
Copper Catalyst ◽  
High Yield ◽  
Sonogashira Coupling ◽  
Terminal Alkynes ◽  
Acid Chlorides ◽  
Triflic Acid ◽  
One Pot

Herein, we report an efficient method for the synthesis of (Z)-β-halovinyl ketones through a one-pot Sonogashira coupling and hydrohalogenation reaction promoted by palladium-copper catalyst and Brønsted acid. The ynone intermediates are generated in situ from readily available acid chlorides and terminal alkynes at room temperature, which are directly converted to (Z)-β-halovinyl ketones by treating with triflic acid. This method avoids the use of an external halogen source and features broad substrate scope, high yield, and good to excellent stereoselectivity.

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