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. Author manuscript; available in PMC: 2009 Aug 21.
Published in final edited form as: Org Lett. 2008 Jul 19;10(16):3485–3488. doi: 10.1021/ol801264u

Table 2.

Direct comparison of condensation reaction conditions.

reaction conditions
product Tf2O (1.2 equiv) 2-ClPyr (This work)a POCl3 (3.0 equiv) (Ref2a)b Oxalyl Chloride (1.1 equiv) FeCl3 (Ref2d)c Tf2O (5.0 equiv) DMAP (Ref2c)d
graphic file with name nihms-108650-t0009.jpg 95% 23% 15% 71%
graphic file with name nihms-108650-t0010.jpg 63% 0% 9% 42%
graphic file with name nihms-108650-t0011.jpg 86% 10% 0% 63%
a

See Figure 1 for reaction conditions.

b

POCl3 (3.0 equiv), xylenes, 150 °C, 3 h.

c

1) Oxalyl chloride (1.1 equiv); FeCl3 (1.2 equiv), CH2Cl2, 23 °C, 12 h. 2) MeOH–H2SO4 (19:1), 65 °C, 1 h.

d

Tf2O (5.0 equiv), DMAP (3.0 equiv), CH2Cl2 23 °C, 16 h.