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. Author manuscript; available in PMC: 2008 Sep 15.
Published in final edited form as: J Am Chem Soc. 2007 Jul 21;129(32):9868–9878. doi: 10.1021/ja072446m

Table 5.

Effect of Brønsted base on cycloisomerization with different catalysts

graphic file with name nihms-62600-t0056.jpg
entry cat (mol%) % conversion of 39ba (no base) % conversion of 39ba (with TTBPb)
1 TfOH (10) 100c <1d
2 Cu(OTf)2 (5) 100e 100e
3 PdCl2(MeCN)2 (5) 100e 100e
4 AgOTf (5) 100e 100e
5 PtCl2 (5) 100f 100f
6 AuCl3 (5) 100e 100e
a

based on GC analysis. Yields comparable to that reported in Table 2.

b

1.5 eq (vs catalyst) 2,4,6-tri-tertbutylpyrimidine (TTBP) added.

c

reaction complete after 6 hours.

d

reaction checked after 24 hours.

e

reaction complete within 30 minutes.

f

reaction complete within 3.5 hours.