. 2022 Oct 3;24(40):7315–7319. doi: 10.1021/acs.orglett.2c02766

Table 1. Optimization of the Reaction Conditions^a.

graphic file with name ol2c02766_0004.jpg

					yield (%)^b
entry	solvent	ammonium salt	base	conversion (%)	2a	3a
1	toluene	PhMe₃NI	KOH	81	56	19
2	toluene	PhMe₃NI	NaOH	43	11	7
3	toluene	PhMe₃NI	LiOH·H₂O	28	6	0
4	toluene	PhMe₃NI	Cs₂CO₃	91	85	5
5	toluene	PhMe₃NI	no base	7	0	0
6	toluene	Me₄NF	Cs₂CO₃	97	26	24
7	toluene	Me₄NCl	Cs₂CO₃	73	67	3
8	toluene	Me₄NBr	Cs₂CO₃	31	23	0
9	toluene	Me₄NI	Cs₂CO₃	8	4	0
10	toluene	PhMe₃NCl	Cs₂CO₃	96	78	7
11	toluene	PhMe₃NBr	Cs₂CO₃	99	78	11
12	t-BuOH^c	PhMe₃NI	Cs₂CO₃	79	65	7
13	CPME	PhMe₃NI	Cs₂CO₃	94	74	7
14	anisole	PhMe₃NI	Cs₂CO₃	89	73	5

Reactions were performed on a 0.35 mmol scale, with 2 equiv of the base and 2 equiv of the ammonium salt under an Ar atmosphere at 120 °C with a reaction time of 18 h.

Yields were determined by quantitative ¹⁹F NMR using trifluoro toluene as the internal standard.

At 100 °C.

Table 1. Optimization of the Reaction Conditionsa.

Table 1. Optimization of the Reaction Conditions^a.