Table 1.

Organocatalytic α-sulfenylation of 1a–1e with 1-benzylsulfanyl[1,2,4]triazole 2a and Lewis bases 4a–4d.

substrate	solvent	temp., °C	time, hr	catalyst	eq. of 2a	yield,a %
1a	CH2Cl2	rt	120	4a	5.0	46
1a	Toluene	rt	120	4a	5.0	44
1a	CH2Cl2	rt	120	4d	10.0	55
1b	CH2Cl2	rt	48	4d	2.0	93
1b	Toluene	rt	24	4c	2.0	95
1b	Toluene	−10	24	4c	1.5	90
1b	Toluene	−78	24	4c	1.5	20
1b	Toluene	−10	24	4a	2.0	94
1b	Toluene	−10	24	4b	2.0	91
1cb	Toluene	rt	72	4a	2.6	10
1cb	Toluene	−10	72	4a	2.6	10
1db	Toluene	rt	72	4a	2.6	10
1e	Toluene	rt	72	4a	2.6	c

^aYield of purified product after chromatographic separation.

^b3b was obtained as the product.

^cNo product was formed, as observed by ¹H NMR.