. 2023 Feb 7;25(6):1020–1024. doi: 10.1021/acs.orglett.3c00221

Table 1. Optimization of the Reaction of Ynamide 1a and Allylsilane 2a^a.

entry	initiator (mol %)	2a (equiv)	solvent	yield^b (%)
1	TMSNTf₂ (10)	2	DCE	50
2	HNTf₂ (10)	2	DCE	35
3	TMSOTf (10)	2	DCE
4	TMSNTf₂ (10)	4	DCE	54
5	HNTf₂ (10)	4	DCE	65
6	TMSNTf₂ (5)	4	DCE	56
7	HNTf₂ (5)	4	DCE	66, 71^c
8	HNTf₂ (5)	4	DCM	64
9	HNTf₂ (5)	4	Et₂O	16
10	HNTf₂ (5)	4	toluene	28
11	HNTf₂ (5)	4	THF
12	HNTf₂ (5)	4	CH₃CN

1a (0.1 mmol, 1 equiv), 2a (equiv), initiator (mol %), solvent (0.4 M).

Isolated yield after flash chromatography purification on silica gel.

2 mmol scale.

Table 1. Optimization of the Reaction of Ynamide 1a and Allylsilane 2aa.