Table 1.

Optimization of Alkenylation of 4-Pyridylmethyl Ethyl Ether with 2-Bromoprop-1-ene 2a^a, ^b

	Pd source	L	Pd/L (mol %)	base	assay yield (%)
1	Pd(OAc)2	L1	10/15	LiN(SiMe3)2	78
2	Pd(OAc)2	L2	10/15	LiN(SiMe3)2	60
3	Pd(OAc)2	L3	10/15	LiN(SiMe3)2	59
4	Pd(OAc)2	L4	10/15	LiN(SiMe3)2	49
5	Pd(OAc)2	L1	2.5/3.75	LiN(SiMe3)2	75
6	[PdCl(allyl)]2	L1	2.5/3.75	LiN(SiMe3)2	74
7	Pd(dba)2	L1	2.5/3.75	LiN(SiMe3)2	88
8	Pd(dba)2	L1	2.5/5.0	LiN(SiMe3)2	88
9	Pd(dba)2	L1	2.5/2.5	LiN(SiMe3)2	96
10	Pd(dba)2	L1	2.5/2.5	NaN(SiMe3)2	60
11	Pd(dba)2	L1	1.0/1.0	LiN(SiMe3)2	95(94)c
12	Pd(dba)2	L1	0.5/0.5	LiN(SiMe3)2	77

^aReactions conducted on a 0.1 mmol scale using 1 equiv of 1a, and 1.5 equiv of 2a.

^bAssay yields determined by ¹H NMR spectroscopy of the crude reaction mixtures.

^cIsolated yield after chromatographic purification.