scholarly journals Palladium-Catalyzed Isocyanide Insertion with Allylic Esters: Synthesis of N -(But-2-enoyl)-N -(tert -butyl)benzamide Derivatives via Intramolecular Acyl Transfer Termination

2017 ◽  
Vol 359 (20) ◽  
pp. 3538-3544 ◽  
Author(s):  
Si Chen ◽  
Wan-Xu Wei ◽  
Jia Wang ◽  
Yu Xia ◽  
Yi Shen ◽  
...  
Keyword(s):  
Acyl Transfer ◽  
Tert Butyl ◽  
Palladium Catalyzed ◽  
Allylic Esters ◽  
Benzamide Derivatives

Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation­ of N-Boc Indoles for the Synthesis of 3-Oxoindolines

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3662-3669 ◽  
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen ◽  
Liang-Guang Wang ◽  
Dan Yang ◽  
Zhi Li
Keyword(s):  
Tert Butyl ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Catalyzed Oxidation

The palladium-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles for the synthesis of tert-butyl 2-hydroxy(methoxy)-3-oxoindoline-1-carboxylates and their derivatives is developed. The process occurs readily using PdCl2 as the catalyst and acetonitrile as the solvent to afford 3-oxoindolines in moderate to high yields. A mechanism for this Pd-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles is proposed.

Palladium-catalyzed synthesis of 4H-benzo[d][1,3]oxazin-4-ones and N-(2-cyanophenyl)benzamides via tert-butyl isocyanide insertion

2015 ◽  
Vol 56 (18) ◽  
pp. 2349-2354 ◽  
Author(s):  
Jin-Mei Wang ◽  
Xiao Jiang ◽  
Ying Zhang ◽  
Yong-Ming Zhu ◽  
Jing-Kang Shen
Keyword(s):  
Tert Butyl ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Chemoselective Synthesis of Indane-1,3-dione Derivatives via tert-Butyl Isocyanide Insertion.

ChemInform ◽  
2015 ◽  
Vol 46 (43) ◽  
pp. no-no
Author(s):  
Huaqing Duan ◽  
Zhong Chen ◽  
Li Han ◽  
Yulin Feng ◽  
Yongming Zhu ◽  
...  
Keyword(s):  
Tert Butyl ◽  
Chemoselective Synthesis ◽  
Palladium Catalyzed

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.

Palladium-Catalyzed C(sp3)–H Nitrooxylation with tert-Butyl Nitrite and Molecular Oxygen

2020 ◽  
Vol 22 (24) ◽  
pp. 9719-9723
Author(s):  
Bo Li ◽  
Ye-Qiang Han ◽  
Xu Yang ◽  
Bing-Feng Shi
Keyword(s):  
Molecular Oxygen ◽  
Tert Butyl ◽  
Palladium Catalyzed

Palladium-Catalyzed Synthesis of Biaryl Ketones via tert-Butyl Isocyanide Insertion

Synlett ◽  
2014 ◽  
Vol 25 (10) ◽  
pp. 1425-1430 ◽  
Author(s):  
Yongming Zhu ◽  
Zhong Chen ◽  
Huaqing Duan ◽  
Xiao Jiang ◽  
Jinmei Wang ◽  
...  
Keyword(s):  
Tert Butyl ◽  
Palladium Catalyzed

A Scalable Synthesis of Biaryl Unit of the HIV Protease Inhibitor Atazanavir

2019 ◽  
Vol 17 (1) ◽  
pp. 68-72
Author(s):  
Chapala Vijayalakshmi ◽  
Malavattu G. Prasad ◽  
Naresh K. Katari ◽  
Pedavenkatagari N. Reddy
Keyword(s):  
Protease Inhibitor ◽  
Large Scale ◽  
Cyano Group ◽  
Cost Effective ◽  
Pharmacokinetic Profile ◽  
Hiv Protease ◽  
Tert Butyl ◽  
Palladium Catalyzed ◽  
Scalable Synthesis

Atazanavir is one of the most prescribed HIV-1 protease inhibitors approved by the FDA. It was the first protease inhibitor approved for once-a-day dosing to treat AIDS due to good oral bioavailability and favorable pharmacokinetic profile. This research aims to develop a new synthetic cost effective process for biaryl-hydrazine unit {tert-butyl 2-[4-(2-pyridinyl)benzyl]hydrazinecarboxylate} of atazanavir on a large scale. The synthesis involved palladium catalyzed Suzuki-Miyaura coupling of 2-chloropyridine and (4-cyanophenyl)boronic acid followed by DIBAL-H reduction of cyano group to aldehyde which is then treated with tert-butyl carbazate to furnish hydrazone subsequently in situ reduction with NaBH4. A large scale synthesis of biaryl-hydrazine unit of atazanavir was accomplished in three steps with 71% overall yield. We have developed a short and efficient synthesis of atazanavir key intermediate biaryl-hydrazine unit. The process does not require the usage of Grignard reagent, expensive catalyst, protection/deprotection of aldehyde moiety and catalytic hydrogenation.

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