Optimization of conditions for defluorinative alkylation of 1-(benzyloxy)-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene (1aa) with cyclohexylboronic acid (2a)^a.

Entry	Deviation from standard conditions	Yield (%)b
1	None	82 (80c)
2	AR-4 as the activation reagent	70
3	AR-1–AR-3 as the activation reagent	<50
4	0.2 equiv. of AR-5	34
5	1.0 equiv. of AR-5	95
6	1.5 equiv. of AR-5	94
7	2.0 equiv. of AR-5	97
8	No photocatalyst	NR
9	No activation reagent	NR
10	No light	NR
11	In air	32

^aStandard conditions: 1aa (0.2 mmol), 2a (0.4 mmol), photocatalyst (0.004 mmol), activation reagent (0.1 mmol), ethyl acetate (EA, 2 mL), Ar, 36 W blue LED, rt, 16 h.

^bYields were determined by ¹⁹F NMR spectroscopy with fluorobenzene as an internal standard. NR = no reaction.

^cIsolated yield.