. Author manuscript; available in PMC: 2013 Mar 21.

Published in final edited form as: Eur J Inorg Chem. 2009 Jun 30;2009(23):3421–3430. doi: 10.1002/ejic.200900279

Table 2.

Three-component coupling of benzaldehyde, piperidine and phenylacetylene catalyzed by water-soluble gold compounds (6-8).

Run ^[a]	Catalyst	Co- catalyst	Temp. (°C)	Time (h)	Yield (%)	Conv. (%)^[b]
1	6 (1 mol%)	---	100	12	17	54
2	6 (5 mol%)	---	100	17	62	44
3	6 (5 mol%)	---	40	42	71	100
4	6 (5 mol%)	NaPF₆ (5 mol%)	100	12	78	56
5	6 (5 mol%)	---	RT	42	81	98
6	6 (2.5 mol%)	NaPF₆ (5 mol%) TPPTS (5 mol%)	100	12	78	56
7	7 (5 mol%)	---	100	17	99	85
8	7 (7 mol%)	---	RT	42	12	70
9	8 (5 mol%)	NaPF₆ (5 mol%)	100	12	94	93
10	8 (5 mol%)	NaPF₆ (5 mol%)	50	24	48	91
11	8 (5 mol%)	NaPF₆ (5 mol%)	40	21	25	88
12	8 (7 mol%)	---	RT	42	39	97
13	6 (7 mol%)	NaPF₆ (7 mol%)	RT	42	75	96
14	RP^a (run 13)	---	RT	42	65	83
15	RP^a (run 14)	---	RT	42	53	77
16	RP^a (run 15)	---	RT	42	38	85
17	6 (7 mol%)	---	RT	93	91	87
18	RP^a (run 17)	---	RT	42	88	85
19	RP^a (run 18)	---	RT	42	83	80
20	RP^a (run 19)	---	RT	42	77	74

^[a]

RP: recycled water phase containing the gold catalyst.

^[b]

Determined by ¹H NMR analysis of crude reaction mixture based on benzaldehyde conversion.