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. Author manuscript; available in PMC: 2010 May 1.
Published in final edited form as: Adv Synth Catal. 2009 May 1;351(7-8):1101–1114. doi: 10.1002/adsc.200800765

Table 3.

Optimization of conditions for arylative cyclization of 1a.

graphic file with name nihms148089u3.jpg
# [Pd] source Ligand Base Temperature 12a:13a Ratioa Yield of 12a, %b
1 Pd(OAc)2 dppp KOAc 120 - 0
2 Pd(OAc)2 dppe KOAc 120 - 0
3 Pd(OAc)2 Ph2P(CH2)5PPh2 KOAc 120 - 0
4 Pd(OAc)2 dppf KOAc 100 90:10 10
5 Pd(OAc)2 d-t-Bupf KOAc 100 90:10 12
6 Pd(OAc)2 d-i-Prpf KOAc 120 95:5 12
7 Pd(OAc)2 d-i-Prpf Cs2CO3 120 - 0
8 Pd(OAc)2 d-i-Prpf Et3N 120 99:1 45
9 Pd(OAc)2 d-i-Prpf EtN(i-Pr)2 120 100:0 60
10 PdCl2 d-i-Prpf EtN(i-Pr)2 120 100:0 31
11 Pd(dba)2 d-i-Prpf EtN(i-Pr)2 120 100:0 20
12 PdCl2(CH3CN)2 d-i-Prpf EtN(i-Pr)2 120 100:0 30
13 Pd(OAc)2 d-i-Prpf Bu4NBr 120 100:0 20
14 Pd(OAc)2 d-i-Prpf DABCO 100 100:0 70c
15 Pd(OAc)2 dppf DABCO 110 100:0 81
16 Pd(OAc)2 d-t-Bupf DABCO 110 100:0 80
17 Pd(OAc)2 d-i-Prpf DABCO 110 100:0 95
18 Pd(OAc)2 d-i-Prpf DABCO 120 100:0 89d
a

Product ratios determined by GC/MS analysis.

b

Yield determined by GC/MS analysis.

c

Yield after 24 hrs.

d

Isolated yield after 6 hrs.