Table 2.

Secondary Amidine Formation.

entry	ynamides	aminesa	amidine products	yield [%]b
1	8a 8c 8d 8e		19: R = TIPS 20: R = t-Bu 21: R = (CH2)3OTBS 22: R = 2-MeO-Ph	≥95
2				≥95
3				92
4				37
5	8f		23	39
6	8a 8b 8g		24: R = TIPS 25: R = Ph 26: R = n-hex	≥95
7				≥95
8				≥95
9	8g		27	70
10	8a		28	≥95
11			29	77
12			30a: n = 1 30b: n = 2 30c: n = 3	≥95
13				≥95
14				≥95
15			31	91
16			32	≥95
17			33a: R = CH3 33b: R = Ph	≥95
18				≥95
19			34	≥95
20			35	82

^aAll reactions utilized 5.0 equiv of the amine, 5.0 mol % PdCl₂(PPh₃)₂, and 1.0 equiv K₂CO₃; and were run in THF [conc = 0.05 M] at 80 °C over 5–8 h.

^bIsolated yields.