Table 1.

Annulation reaction condition optimization ^a.

Entry	Additive (%)	Solvent	Temp. (°C)	Yield (%) b
1	Cu(OAc)2 (10)	DMF	120	55
2	Cu (NO3)2(10)	DMF	120	-
3	CuCl2 (10)	DMF	120	10
4	CuBr2 (10)	DMF	120	22
5	Cu(CF3SO3)2 (10)	DMF	120	44
6	NaOAc (10)	DMF	120	0
7	CsOAc (10)	DMF	120	0
8	Cu(OAc)2 (10)	DMF	120	50 c
9	-	DMF	120	0
10	Cu(OAc)2 (20)	DMF	120	46
11	Cu(OAc)2 (5)	DMF	120	19
12	Cu(OAc)2 (10)	DMF	100	63
13	Cu(OAc)2 (10)	DMF	80	52
14	Cu(OAc)2 (10)	DMF	140	32
15 d	Cu(OAc)2 (10)	DMF	100	71
16 e	Cu(OAc)2 (10)	DMF	100	58
17 f	Cu(OAc)2 (10)	DMF	100	42
18 g	Cu(OAc)2 (10)	DMF	100	32
19 h	Cu(OAc)2 (10)	DMF	100	56
20	Cu(OAc)2 (10)	MeCN	100	13
21	Cu(OAc)2 (10)	H2O	100	0
22	Cu(OAc)2 (10)	MeOH	100	32
23	Cu(OAc)2 (10)	PEG-400	100	46
24 i	Cu(OAc)2 (10)	DMF	100	0 (Pd(OAc)2)
25 j	Cu(OAc)2 (10)	DMF	100	0 (PdCl2)
26 k	Cu(OAc)2 (10)	DMF	100	64 (Ru 10%)
27 l	Cu(OAc)2 (10)	DMF	100	22 (Ru 2%)

Reaction conditions: ^a 1a (1 mmol), 2a (1.0 mmol), [Ru(p-cymene) Cl₂]₂ (5 mol%), additive (10 mol%), and solvent (3 mL), 12 h. ^b Isolated yield. ^c Additional 10% of KBF₄. ^d 1.5 mmol of 2a. ^e 2.0 mmol of 2a. ^f 0.8 mmol of 1a. ^f 6 h. ^g 24 h. ^h 24 h. ⁱ Pd(OAc)₂ instead of [Ru(p-cymene) Cl₂]₂. ^j PdCl₂ instead of [Ru(p-cymene) Cl₂]₂. ^k 10 mol% of [Ru(p-cymene) Cl₂]₂. ^l 2 mol% of [Ru(p-cymene) Cl₂]₂.