Microwave-assisted chemoselective reduction of conjugated nitroalkenes to nitroalkanes with aqueous tri-n-butyltin hydride

Figures & data

Scheme 1. Chemoselective microwave reduction of α,β-unsaturated nitro compounds.

Table 1. Microwave reduction of nitroalkenes

Entry	2-3	R1	R2	Time (min)	Yield of 3 (%)
1	a	C6H5	H	10	95
2	b		H	15	92
3	c	4-NO2C6H4	H	10	86
4	d	2-furfuryl	H	8	82
5	e	2-thiophenyl	H	8	79
6	f	n-C6H13	H	10	73
7	g	Cyclohexyl	H	10	75
8	h	C6H5	CH3	20	82
9	i		CH3	25	76
10	j	4-NO2C6H4	CH3	16	85
11	k	2-furfuryl	CH3	12	72
12	l	n-C6H13	CH3	10	68
13	m	Cyclohexyl	CH3	10	74
14	n	C6H5	C6H5	18	82
15	o	2-thiophenyl	C6H5	15	75
16	p	n-C6H13	C6H5	20	92
17	q	C6H5	C6H4CH2	22	84
18	r	2-thiophenyl	C6H4CH2	20	78
19	s	C6H13	C6H4CH2	20	92

Scheme 2. Chemoselective microwave reduction of 1-substituted-2-nitro-1-cyclohexenes.

Table 2. Microwave reduction of 1-substituted-2-nitro-1-cyclohexenes to 1-substituted -2-nitrocyclohexanes

Entry	2-3	R	Time (min)	Yield of 3 (%)
20	t	H	25	94
21	u	CH3	25	86
22	v	n-C5H11	30	78
23	w	Ph	30	82

Scheme 3. Probable mechanism for the reduction of nitroalkenes.