Table 1.

Optimization of the Csp³-F bond transformation with lithium iodide^a

Entry	Substrate	Solvent	Time (h)	Product	Yield (%)
1	1	CH2Cl2	6	3	99
2	1	CH2Cl2	6	3	80b
3	1	CHCl3	24	3	99
4	1	ClCH2CH2Cl	24	3	99
5	1	DMF	48	3	0
6	1	DMSO	48	3	0
7	1	CH3CN	48	3	0
8	1	NMP	48	3	0
9	1	1,4-dioxane	48	3	0
10	1	Et2O	48	3	0
11	1	MeOH	48	3	0
12	1	EtOH	48	3	0
13	1	pyridine	48	3	0
14	1	benzene	48	3	98
15	1	toluene	48	3	65
16	1	toluene	6	3	99c
17	1	neat	18	3	99d
18	2	CH2Cl2	48	4	99
19	2	CH2Cl2	5	4	99e
20	2	toluene	21	4	99
21	2	toluene	24	4	94e
22	2	toluene	6	4	93c

^aConditions: 1 (0.2 mmol), LiI (0.4 mmol) in 0.4 mL solvent at 25 °C.

^b1.2 equiv. of LiI used,

^cThe reaction was carried out at 60 °C,

^dThe reaction was carried out in the absence of solvent with 3.0 equivalent of LiI,

^e1.0 equivalent of TEMPO was added.