Table 1.

Optimization of reaction conditions.^[a]

entry	solvent A	solvent B	base	yield (%)[b]
1	CH2Cl2	THF	KOtBu	5
2	CH2Cl2	THF	LHMDS	35
3	CH2Cl2	THF	nBuLi	42
4	Acetone	THF	nBuLi	21
5	EtOAc	THF	nBuLi	10
6	EtCN	THF	nBuLi	52
7	EtCN	Et2O	nBuLi	43
8	EtCN	PhMe	nBuLi	71 (70)

^[a]Reaction conditions: naphthalene (5, 1.0 mmol, 2.0 eq.), MTAD (1, 0.5 mmol, 1.0 eq.), solvent A (0.1 M), visible light, −50 °C; then addition of solution of acetophenone oxime (1.0 mmol, 2.0 eq.) and base (0.95 mmol, 1.9 eq.) in solvent B; and Pd(PPh₃)₄ (5.0 mol%), −50 to 0 °C, 5 h.

^[b]Determined by ¹H NMR analysis relative to the internal standard. Isolated yield shown in parentheses. THF=tetrahydrofuran, LHMDS=lithium bis(trimethylsilyl)amide