Table 1.

Reaction conditions optimization.^[a]

Entry	Deviation from the optimized conditions	Yield(%)[b]
1	-	77
2	DCE/H2O (4:1) as reaction media	69
3	PhCF3/H2O (4:1) as reaction media	67
4	PhCH3/H2O (4:1) as reaction media	0
5	NaBARF instead of AgNTf2 as chloride abstractor	70
6	AgOTf instead of AgNTf2 as chloride abstractor	70
7	AgBF4 instead of AgNTf2 as chloride abstractor	61
8	2 equiv of 1a; DCE/H2O (4:1) as reaction media	56
9	Ph3P, IPr, JohnPhos or MorDalPhos as Au ligand; 2 equiv of 1a; DCE/H2O (4:1) as reaction media	≤6
10	JohnPhos as Au ligand, 2 equiv of 1a; DCE/H2O (4:1) as reaction media; 5% Et3N	16
11	L3 as Au ligand; 2 equiv of 1a; DCE/H2O (4:1) as reaction media	37
12	L4 as Au ligand; 2 equiv of 1a; DCE/H2O (4:1) as reaction media	18
13	dry DCM used as solvent	0
14	(E)-styrylboronic acid instead of 1a	35[c]
15	(Z)-1a instead	0[d]

^[a]0.1 mmol of 1-hexyn-3-ol (2) were used.

^[b]NMR yields.

^[c]27% 2 remained along with 22% of hydration product.

^[d]Mostly protodeboronation.