Table 2.

Zinc chalcogenates 1–3 in the preparation of chalcogenol esters.

Entry	Reagent	Medium	Time (h)	Yield (%) a	ae (%) b	Reference
1	PhSeZnCl	THF	24	25	66	[50]
2	PhSeZnBr	THF	24	30	60	[50]
3	[PhSeZnSePh] 1	THF	3	32 c	79.6	[56]
4	[PhSeZnSePh] 1	THF	3	40 d	79.6	–
5	PhSZnBr	THF	24	86	54.6	[57]
6	[PhSeZnSePh/PhSeH]	HClacq/Et2O	4	38	–	[56]
7	PhSeZnCl	H2O	3	60	66	[50]
8	PhSeZnBr	H2O	3	70	60	[50]
9	PhSZnBr	H2O	3	65	54.6	[57]
10	[PhSeZnSePh] 1	H2O	0.5	83	79.6	–
11	[PhSeZnSePh]TMEDA 3	H2O	0.5	66	77	–
12	[PhSZnSPh] 2	H2O	0.5	50	76	–

^a Conversion estimated by NMR; ^b Atom economy = m.w. of final product × 100/Σ (m.w. reactants); ^c 1 was prepared in the presence of 10 mol % of TfOH. Compound 5a was formed together with 34% PhC(O)O(CH₂)₄SePh and 28% PhC(O)O(CH₂)₄ O(CH₂)₄SePh; ^d 1 was prepared in the presence of 10 mol % of TFA. Compound 5a was formed together with 27% PhC(O)O(CH₂)₄SePh and 5% PhC(O)O(CH₂)₄ Cl.