Pd/C Catalyzed Decarboxylation-Transfer Hydrogenation of Quinoline Carboxylic Acids

2020 ◽  
Vol 17 ◽  
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen
Keyword(s):  
Carboxylic Acids ◽  
Reaction System ◽  
Ammonium Formate ◽  
Transfer Hydrogenation

Abstract:: Pd/C catalyzed decarboxylation-transfer hydrogenation of quinoline carboxylic acids and transfer hydrogenation of quinolines had been developed for the synthesis of 1,2,3,4-tetrahydroquinolines. These two processes were implemented smoothly using Pd/C (0.9 mol%) as catalyst with ammonium formate as hydrogen source in ethanol at 80 oC. The reaction system also can be applied to transfer hydrogenation of benzo[h]quinoline and 2,9-dimethyl-1,10-phenanthroline with good to excellent yields. And the gram scale and recycling of catalyst had been tested with good results. Furtherly, the mechanism of Pd/C catalyzed reduction of quinoline carboxylic acids and quinolines had been proposed.

Hydroxycarbonylation of Alkenes with Formic Acid Using Rhodium Iodide complex and Alkylammonium Iodide

2021 ◽  
Author(s):  
Okada Masaki ◽  
Katsuhiko Takeuchi ◽  
Kazuhiro Matsumoto ◽  
Tomoharu Oku ◽  
Jun-Chul Choi
Keyword(s):  
Environmental Impact ◽  
Formic Acid ◽  
Carboxylic Acids ◽  
Reaction System ◽  
Iodide Complex

Hydroxycarbonylation of alkenes using formic acid (HCOOH) is ideal for the synthesis of various carboxylic acids as a means to develop a sustainable reaction system with lower environmental impact. In...

scholarly journals Ruthenium Hydride Catalyzed Direct Oxidation of Alcohols to Carboxylic Acids via Transfer Hydrogenation: Styrene Oxide as Oxygen Source

Synlett ◽  
2012 ◽  
Vol 24 (01) ◽  
pp. 90-96 ◽  
Author(s):  
Majid Moghadam ◽  
Abbas Rahmati ◽  
Behjat Barati ◽  
Shahram Tangestaninejad ◽  
Valiollah Mirkhani ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Styrene Oxide ◽  
Transfer Hydrogenation ◽  
Direct Oxidation ◽  
Ruthenium Hydride ◽  
Oxidation Of Alcohols

scholarly journals Study of Hydrogenolytic Cleavage of Peptide-Resin Benzyl Ester Bonds for Synthesis of Protected Fragments of the Human Leukocyte Interferon

1983 ◽  
Vol 38 (8) ◽  
pp. 1022-1024 ◽  
Author(s):  
Anders Ljungqvist ◽  
Karl Folkers
Keyword(s):  
Human Leukocyte ◽  
Benzyl Ester ◽  
Ammonium Formate ◽  
Transfer Hydrogenation ◽  
Palladium Acetate ◽  
Ester Bond ◽  
The Matrix ◽  
Fragment Condensation ◽  
Human Leukocyte Interferon

Three Roe-protected fragments of the human leukocyte interferon, LeIFA, have been synthesized: I, BOC LeIFA (99-105) (BOC-Val-Ile-Gln-Gly-Val-Gly-Val); II, BOC Lei FA (116-119) (BOC-Ile-Leu-Ala-Val); III, BOC LeIFA (123-126) (BOC-Phe-Gln-Arg(Tos)-Ile). The presence of the Boc-group was desired so that these peptides could serve as intermediates in fragment condensation toward larger segments of interferon. To achieve these intermediates, a study was desirable on three methods of cleavage of the benzyl ester-polymer bonds. It was found that hydrogenolysis with hydrogen and palla­dium generated in situ was distinctly superior to transfer hydrogenation with ammonium formate or cyclohexene. An effective swelling of the peptide-resin to allow penetration of palladium acetate into the matrix and mobility of the peptide chains on the resin to expose the bonzyl ester bond to hydrogenolysis appear to be essential conditions for the best cleavage.

Sign in / Sign up

Export Citation Format

Share Document