Glycerol as a recyclable solvent in a microwave-assisted synthesis of disulfides

Figures & data

Scheme 1.  General scheme of reaction.

Table 1. Optimization of oxidation reaction.^a

Entry	Temperature (°C)	Base	Yield of 2a (%)^b
1	30	K2CO3	15
2	50	K2CO3	20
3	80	K2CO3	45
4	100	K2CO3	83
5	120	K2CO3	89
6	150	K2CO3	89
7	120	Na2CO3	92
8	120	Cs2CO3	92
9	120	Na3PO4	56
10	120	K3PO4	80
11	120	KOH	86
12	120	LiOAc	70
13	120	NaOAc	69
14	120	Et3N	82
15	120	–	–
16^c	120	Na2CO3	85
^aReactions are performed in the presence of 1a (1.0 mmol), base (1.1 mmol), glycerol (1 mL) in a microwave reactor (CEM Explorer).
^bYields are given for isolated product.
^cReaction performed using conventional heating for 12 h.

Figure 1.  Plot of conversion vs. time for the oxidation of benzenethiol 1a.

Table 2. Reuse of glycerol.^a

Run	Time (minutes)	Yield of 2a (%)^c
1	15	92
2^b	15	92
3^b	15	90
4^b	20	89
5^b	30	88
^aReaction was performed in the presence of benzenethiol 1a (1.0 mmol), Na2CO3 (1.1 mmol), glycerol (1 ml), at 120°C in a microwave reactor.
^bRecovered glycerol was used.
^cYields are given for isolated products.

Table 3. Scope and generality of the synthesis of disulfides 2a–t using glycerol as solvent.^a

Entry	Product (Ref.)	Yield (%)^b	Entry	Product (Ref.)	Yield (%)^b
1		92	11		85
	2a 14			2k 23
2		87	12		88
	2b 15			2l 24
3^c		87	13
	2c 16			2m 25	89
4		91	14^c		87
	2d 17			2n 17
5		92	15^c		86
	2e 18			2o 26
6		88	16^c		84
	2f 19			2p 27
7		89	17^c
	2g 17			2q 28	86
8		93	18^c		82
	2h 20			2r 29
9		92	19^c		81
	2i 21			2s 21
10^c		92	20		81
	2j 22			2t 30
^aReactions are performed in the presence of thiol (1.0 mmol), Na2CO3 (1.1 mmol), glycerol (1 mL), at 120°C in a microwave reactor for 15 minutes.
^bYields are given for isolated product.
^cReactions are performed in 30 minutes.

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