Table 1. Optimization of Silver-Catalyzed Propargylation Reaction.

entry	deviation from standard conditions	yielda (%)	erb
1	none	51	99:1
2c	catalyst preformed in MeOH and reaction run in THF	19	96:4
3	Walphos-8 instead of Walphos-1	35	76:24
4	Josiphos-6 instead of Walphos-1	70	74:26
5	(S)-BINAP instead of Walphos-1	55	40:60
6	reaction performed at 4 °C	54	99:1
7	reaction performed at rt	57	98:2
8	reaction performed at rt with 4 equiv 2	76	99:1

^aDetermined using ¹H NMR by comparison to PhTMS as internal standard.

^bDetermined using chiral SFC.

^cPreparation of Ag/Walphos catalyst performed according to ref (10b).