Table 1.

Optimization of Conditions for Heck Annulation^a

entry	palladium	additive	base	temp (°C)	yield (%)b
1c	Pd(OAc)2	–	Ag2CO3	66	<5
2	Pd(OAc)2	–	Et3N	82	<5
3	Pd(Ph3P)4	nBu4NCl	K2CO3	82	0
4	Pd2(dba)3	nBu4NCl	K2CO3	82	0
5	Pd2(dba)3·CHCl3	nBu4NCl	K2CO3	82	54
6	Pd(OAc)2	nBu4NCl	K2CO3	82	62
7	Pd(OAc)2	nBu4NCl	Ag2CO3	82	0
8	Pd(OAc)2	nBu4NCl	NaHCO3	82	80
9	Pd(OAc)2	nBu4NCl	Et3N	82	74
10	Pd(OAc)2	nBu4NCl	PMPd	82	59

^aReaction conditions: 6 (0.5 mmol), Pd(OAc)₂ (10 mol %), PPh₃ (20 mol %), nBu₄NCl (0.5 mmol), base (1 mmol), CH₃CN (10 mL), under Ar.

^bIsolated yield.

^cReaction in THF.

^d1,2,2,6,6-Pentamethyl piperidine.