In Quest of “Stereoselective Switch” for On-Water Hydrothiolation of Terminal Alkynes Using Different Additives and Green Synthesis of Vicinal Dithioethers

Table 2

Hydrothiolation of aryl thiol [B] to aryl acetylene [A] in (1.1 : 1) in water at room temperature.

Entry	[A]	[B]	Time (h)	Yield^a (%) [C]	E/Z [C]^b
1	R^1 = H	R^2 = H	2.0	85	22 : 78
2	R^1 = CH3	R^2 = H	3.5	91	40 : 60
3	R^1 = CH3	R^1 = CH3	2.5	88	29 : 71
4	R^1 = H	R^1 = OCH3	3.0	93	12 : 88
5	R^1 = CH3	R^1 = OCH3	2.0	90	22 : 78
6	R^1 = H	R^2 = F	2.0	88	80 : 20
7	R^1 = CH3	R^2 = F	2.0	94	39 : 61

aYield represents the product [C] after purification by column chromatography. bE/Z ratio was determined by ¹H NMR of the crude mixture.