Table 1.

Solvent screening for the coupling of benzenediazonium tetrafluoroborate (1a) and CS₂ (2).^a

Entry	Solvents	Yield 3a (%)b	Yield 4a (%)b	Yield 5a (%)b
1	MeOH	n.d.	n.d.	n.d.
2	THF	36	5	n.d.
3	dioxane	n.d.	14	n.d.
4	acetone	n.d.	n.d.	n.d.
5	DCM	n.d.	n.d.	19
6	acetonitrile	n.d.	n.d.	n.d.
7	DMF	54	3	31
8	DMSO	53	3	27
9	hexane	n.d.	n.d.	24

^aReaction conditions: 1a (0.1 mmol), 2 (0.2 mmol), solvent (2 mL), rt, 6 h; ^byields were determined by HPLC using 3a and 4a as the external standards; the yield of 5a is based on the integration of the corresponding HPLC peaks [17–18]; n.d. = not determined.