Novel Sc(OTf)₃/3-HQD Catalyst for Morita–Baylis–Hillman Reaction

Figures & data

Scheme 1 Morita–Baylis–Hillman reaction.

Table 1. Effect of base on the MBH reaction ^a

Entry	Lewis base	Time (h)	Yield (%) ^b
1	Imidazole	24	30
2	Et3N	24	23
3	Pyridine	24	—
4	3-HQD	3	59
5	DMAP	24	44

Table 2. MBH reactions of p-nitrobenzaldehyde (1.0 equiv.) with methyl acrylate (3.0 equiv.) in the presence of Sc(OTf)₃ and 3-HQD

Entry	Sc(OTf)3 (mol %)	3-HQD (mol %)	Solvent	Temperature (°C)	Time (h)	Yield (%) ^a
1	0	50	CH3CN	20	3	59
2	5	10	CH3CN	20	3	52
3	5	20	CH3CN	20	1	78
4	5	50	CH3CN	20	1	79
5	5	20	CH2Cl2	20	1	66
6	5	20	Toluene	20	1	71
7	5	20	H2O	20	1	<10
8	5	20	DMF	20	50 min	84
9	5	20	THF/H2O (1:1)	20	1	66
10	5	20	DMF/H2O (1:1)	20	1	62
11	5	20	DMF	0	3	44
12	5	20	DMF	40	50 min	88

Table 3. Sc(OTf)₃/3-HQD cocatalyzed the MBH reaction ^a

Entry	Products	Time (h)	Yield (%) ^b
1		8	73
2		9	70
3		9	73
4		36	30
5		36	23
6		6	79
7		8	74
8		4	82
9		50 min	92
10		1	88
11		10 min	98
12		3	88
13		4	88
14		1.5	90
15		1	88
16		1	88
17		40 min	92