. 2021 Aug 13;6(33):21595–21603. doi: 10.1021/acsomega.1c02825

Table 1. Catalyst- and Additive-Free Thermal or Photochemical Decomposition of Benzenediazonium Tetrafluoroborate (1a) in Different Solvents^a.

entry	solvent	condition A (2a/3a, %)^b	condition B (2a/3a, %)^b
1	H₂O	0/0	0/0
2^c	MeOH	13/4	17/7
3^c	EtOH	22/n.d.	10/n.d.
4^c	acetone	20/3	17/3
5	CH₃CN	13/0	10/0
6	DMF	7/8	10/0
7	DMSO	5/0	2/0
8	EtOAc	45/0	23/2
9	n-BuOAc	55/0	42/3
10	Et₂O	27/0	23/0
11	1,4-dioxane	62/0	19/3
12	THF	48/6	0/80
13	DME	40/4	7/66
14	diglyme	34/5	10/62
15	CH₂Cl₂	86/10	56/11
16	DCE	91/4	72/2
17	CHCl₃	86/14	70/10
18	benzene	87/n.d.	70/n.d.
19	toluene	91/5	70/4
20	p-xylene	93/0	56/4
21	m-xylene	96/0	67/3
22	PhCl	97/0	68/0
23	PhCF₃	85/0	68/0
24	hexane	85/0	75/0
25	none	43/0	32/0

Condition A: a mixture of 1a (0.5 mmol) and solvent (2 mL) was heated at 60 °C in a sealed tube under an air atmosphere for 16 h. Condition B: a mixture of 1a (0.5 mmol) and solvent (2 mL) was irradiated by blue LEDs (435–455 nm) at ambient temperature in a sealed tube under an air atmosphere for 16 h.

Yields were determined by gas chromatography (GC) analysis of the reaction mixtures using hexadecane as an internal standard. “n.d.”: not determined.

Solvents were used as received from commercial sources.

Table 1. Catalyst- and Additive-Free Thermal or Photochemical Decomposition of Benzenediazonium Tetrafluoroborate (1a) in Different Solventsa.

Table 1. Catalyst- and Additive-Free Thermal or Photochemical Decomposition of Benzenediazonium Tetrafluoroborate (1a) in Different Solvents^a.