Electrocatalytic Oxidative Coupling of Primary Amines with the Medium ABNO †

doi:10.7503/cjcu20190330

Abstract

Abstract:

In the NaClO₄-MeCN solution, an electrochemical oxidative coupling of primary amines was developed with the electrocatalytic medium 9-azabicyclo[3.3.1]nonane-N-oxyl(ABNO). The electrocatalytic performance of ABNO for the primary amines was studied by cyclic voltammetry. As compared with 2,2,6,6-tetramethylpiperidine nitroxyl radical under similar conditions, ABNO showed higher electrocatalytic perfor-mance in the oxidation coupling reaction. The Ph—CH＝NH was analyzed as the intermediate by electrochemical in situ FTIR. Under the optimized conditions, a series of aromatic primary amines underwent the electrochemical oxidative coupling to form corresponding imines in good to excellent yields with the ABNO as the electrocatalytic medium.

Key words: 9-Azabicyclo[3.3.1]nonane-N-oxyl, Cyclic voltammetry, in situ FTIR spectrum, Electro-catalysis, Oxidative coupling

CLC Number:

O621

TrendMD:

CAI Yanchao,NIU Pengfei,SHEN Zhenlu,LI Meichao. Electrocatalytic Oxidative Coupling of Primary Amines with the Medium ABNO ^†[J]. Chem. J. Chinese Universities, 2019, 40(11): 2308.

Figures/Tables 9

Scheme 1 Electrocatalytic oxidative coupling of benzylamine with the medium ABNO

Fig.1 Cyclic voltammograms of Pt electrode in 0.1 mol/L NaClO4-MeCN solution with 1.0 mmol benzylamine(a), 0.1 mmol ABNO(b) and 0.1 mmol ABNO+1.0 mmol benzylamine(c) at the scan rate of 50 mV/s

Scheme 2 Mutual transformation of ABNO and ABNO+

Fig.2 Cyclic voltammograms of Pt electrode in 0.1 mol/L NaClO4-MeCN solution with 0.1 mmol TEMPO(a) and 0.1 mmol TEMPO+1.0 mmol benzylamine(b) at the scan rate of 50 mV/s

Fig.3 In situ FTIR spectra collected on Pt electrode in 0.1 mol/L NaClO4-MeCN solution with 0.1 mmol ABNO and 1.0 mmol benzylamine at different potential

Fig.4 In situ FTIR spectra collected on Pt electrode in 0.1 mol/L NaClO4-MeCN solution with 0.1 mmol ABNO and 1.0 mmol benzylamine at 200 mV

Scheme 3 Proposed reaction mechanism for benzylamine to N-benzyl-1-phenylmethanimine

Entry	Catalyst	E/mV	Yield(%)^b	Entry	Catalyst	E/mV	Yield(%)^b
1	ABNO	600	76	6	ABNO^c	800	60
2	ABNO	700	89	7	—	800	Trace
3	ABNO	800	98	8	—	1500	4
4	ABNO	900	94	9	TEMPO	800	80
5	ABNO	1000	94

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