Nature Communications

Table 1 Optimization of reaction conditions with butane-2,3-diyldibenzene^a

From: Electro-oxidative amination of benzylic C(sp³)–C(sp³) bonds in aromatic hydrocarbons


Entry	Electrolyte	E_cell	Acid	Additive	Yield (%)
1	Et₄NBF₄	2.4 V	0.5 mL TFA	–	26
2	LiClO₄	2.4 V	0.5 mL TFA	–	6
3	Et₄NOTs	2.4 V	0.5 mL TFA	–	3
4	Et₄NBF₄	2.6 V	0.5 mL TFA	–	18
5	Et₄NBF₄	2.8 V	0.5 mL TFA	–	18
6	Et₄NBF₄	2.4 V	100 μL TfOH	–	33
7	Et₄NBF₄	2.4 V	100 μL MeSO₃H	–	53
8	Et₄NBF₄	2.4 V	100 μL MeSO₃H	1.0 mL HFIP	79
9^b	Et₄NBF₄	2.4 V	100 μL MeSO₃H	1.0 mL HFIP	83 (80)^c
10	Et₄NBF₄	–	100 μL MeSO₃H	1.0 mL HFIP	0
11 ^d	Et₄NBF₄	2.4 V	100 μL MeSO₃H	1.0 mL HFIP	47
12^e	Et₄NBF₄	2.4 V	100 μL MeSO₃H	1.0 mL HFIP	69
13 ^f	Et₄NBF₄	2.4 V	100 μL MeSO₃H	1.0 mL HFIP	64
14	Et₄NBF₄	i = 10 mA	100 μL MeSO₃H	1.0 mL HFIP	58
15 ^g	Et₄NBF₄	2.4 V	100 μL MeSO₃H	1.0 mL HFIP	71

^aReaction conditions: S1 (0.3 mmol), electrolyte (0.1 M), MeCN (3.0 mL), carbon cloth anode, Pt plate cathode, rt, in an undivided cell with constant voltage for 16 h under air. Yields determined by ¹H NMR analysis using 1,1,2,2-tetrachloroethane as internal standard. ^b11 h. ^cIsolated yield. ^dNi as cathode. ^eStainless steel as cathode. ^fGF020 as anode. ^gMeCN (40 eq.), DCM (2 mL) were used as solvent. DCM Dichloromethane, HFIP 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol, TFA trifluoroacetic acid, TfOH trifluoromethanesulfonic acid, Me methyl, Et ethyl, Ac acetyl.

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