Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/19199
Title: Electrocarboxylation of arylmethyl chlorides catalyzed by cobalt 6,6′-bis(2-hydroxyphenyl)-2, 2′-bipyridine
Authors: Chung, WH
Guo, P
Wong, KY 
Lau, CP
Issue Date: 2000
Publisher: Elsevier
Source: Journal of electroanalytical chemistry, 2000, v. 486, no. 1, p. 32-39 How to cite?
Journal: Journal of electroanalytical chemistry 
Abstract: The electrocatalytic carboxylation of 4-(trifluoromethyl)benzyl chloride, 4-methoxybenzyl chloride and diphenytmethyl chloride in N,N-dimethylformamide (DMF) by [Co(dobpy)] (dobpy = 6,6′-bis(2-hydroxyphenyl)-2,2′-bipyridine dianion) has been investigated. Electrocarboxylation of the arylmethyl chlorides in CO2-saturated DMF solution in the presence of the cobalt catalyst resulted in the formation of a mixture of the corresponding arylacetic acid and substituted toluene. The ratio of carboxylic acid to hydrocarbon in the product mixture was dependent on the nature of the arylmethyl chlorides and the electrolysis potential. Voltammetric studies indicated that the electrogenerated [CoI(dobpy)]- underwent oxidative addition with RCl to give [CoIII(dobpy)R]-. The unstable one-electron-reduced complex [CoII(dobpy)R]- underwent homolytic Co-C bond cleavage to generate R·, which in turn could undergo further reduction to give the carbanion R- either at the electrode or in the solution. On the one hand, R- was trapped by CO2 to produce carboxylic acid; on the other hand, the protonation of R- and hydrogen-atom abstraction by R· would lead to the production of RH. [Co(dobpy)] is a more selective catalyst in the production of carboxylic acid than [Co(TPP)] (TPP = 5,10,15,20-meso-tetraphenylporphine dianion) and a more robust catalyst than [Co(salen)] (salen = N,N′-bis(salicylidene)ethane-1,2-diamine dianion).
URI: http://hdl.handle.net/10397/19199
ISSN: 0022-0728
DOI: 10.1016/S0022-0728(00)00125-X
Appears in Collections:Journal/Magazine Article

Access
View full-text via PolyU eLinks SFX Query
Show full item record

SCOPUSTM   
Citations

13
Last Week
0
Last month
0
Citations as of Oct 15, 2017

WEB OF SCIENCETM
Citations

13
Last Week
0
Last month
0
Citations as of Oct 16, 2017

Page view(s)

48
Last Week
1
Last month
Checked on Oct 16, 2017

Google ScholarTM

Check

Altmetric



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.