A straightforward catalytic approach to obtain deuterated chloroform at room temperature

Author(s)

Higuera-Padilla, Angel Ruben ^[1] ; Kock, Flavio Vinicius Crizostomo ^{[2, 3]} ; Batista, Alzir Azevedo ^[2] ; Colnago, Luiz Alberto ^[1]

Affiliation

^[1] Embrapa Instrumentat, Rua 15 Novembro 1452, BR-13560970 Sao Carlos, SP - Brazil

^[2] Univ Fed Sao Carlos, Sao Carlos - Brazil

^[3] Sao Carlos Inst Chem, Sao Carlos - Brazil

• Document type: Journal article
• Source: Magnetic Resonance in Chemistry; v. 58, n. 10 JUL 2020.
• Web of Science Citations: 0

Abstract

We report the catalytic activity for the complexes-cis-{[}RuCl2(dppb)(bipy)] (A), and {[}eta(6)-(p-cymene)Ru (dppb)Cl]PF6(B), wherein dppb = 1,4-bis(diphenylphosphine)butane, and bipy = 2,2 `-bipyridine-for the synthesis of CDCl(3)from CHCl(3)using D2O as deuterium source. H/D exchange reactions were performed using a chloroform/D2O, 1:2 molar ratio, vigorously stirred, at room temperature. One mole of KOH was dissolved in D2O fraction and catalytic complexes from 0.002 to 0.05 mmol were dissolved in chloroform. The H/D exchange reactions were monitored using(13)C nuclear magnetic resonance sequences without proton decoupling. The reaction using 0.01 mmol of compound A reached approximately 55% of H/D conversion in 1 h. In the same time, the reactions with 0.002 mmol of compound A and without catalyst show approximately 28% and 3% H/D exchange, respectively. Without the catalysts, the H/D exchange was only 12.0% in 5 h. For compound B, 55% H/D conversion was observed in 1 h, only when 0.05 mmol was used, which is much higher catalyst concentration. After the isolation of the chloroform fraction and two more addition of D2O, it was possible to obtain 95.0% H/D exchange in approximately 3 h, using 0.01 mmol of the compound A. Therefore, compound A is an efficient catalyst for a rapid and straightforward synthesis of CDCl(3)from CHCl(3)at room temperature and using D2O as deuterium source. (AU)

• FAPESP's process: 12/23169-8 - In situ study of action of quitosan biopolymer in the decontamination of metals and herbicides in aqueous system by electrochemistry coupled to high and low field NMR
• Grantee: Flavio Vinicius Crizostomo Kock
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 19/13656-8 - Development and application of nuclear magnetic resonance in products and agricultural processes
• Grantee: Luiz Alberto Colnago
• Support Opportunities: Regular Research Grants
• FAPESP's process: 17/02197-7 - Reaction monitoring of deuterated compounds synthesis, with use of metal catalysts, by NMR
• Grantee: Angel Rubén Higuera Padilla
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 18/16040-5 - Biorational control of Pest-Insect
• Grantee: Flavio Vinicius Crizostomo Kock
• Support Opportunities: Scholarships in Brazil - Post-Doctoral