. Author manuscript; available in PMC: 2011 Dec 22.

Published in final edited form as: Tetrahedron Lett. 2010 Dec 22;51(51):6748–6752. doi: 10.1016/j.tetlet.2010.10.087

Table 3.

Effect of catalyst and additives on the yield of benzyl 4-bromo-3,5-bis(benzloxy)benzoate (3)

Entry^a	Catalyst^b	Mole %	Time	1:3:4^c	Yield of 3^d
11	PdCl₂, X-Phos	2,6	30 min	2:1:trace	n/a
12	PdCl₂, X-Phos	(2,6) × 2	30 min × 2	0:1:trace	29
13	PdCl₂, PPh₃	2,6	30 min	2.3:1:trace	n/a
14	PdCl₂, RuPhos	2,6	30 min	1.6:1:0	n/a
15^b	Pd(OAc)₂, dppb	5,5	30 min	0:3:1	n/a
16^b	PdCl₂(dppf)CH₂Cl₂	9	60 min	1:3:1	n/a
17^b	PdCl₂(dppf)CH₂Cl₂	9	90 min	0:5:1	n/a

THF:H₂O (10:1) at 0.051 M, 5 equiv of 2, 3 equiv Cs₂CO₃, 150 °C.

Employed Bu₄NI.

Determined by ¹H NMR integration of the crude mixture.

Isolated yield.