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. Author manuscript; available in PMC: 2014 Feb 15.
Published in final edited form as: J Org Chem. 2013 Jan 24;78(4):1583–1588. doi: 10.1021/jo302696y

Table 1.

Substrate generality in the one-pot production the pyrazoles

graphic file with name nihms-436519-t0002.jpg

entry R1/R2 (1) Ar in 5 8 yield 8(%)b
1 H/Me (1a) 4-MeOC6H4 (5a) 8a 87
2 H/Me (1a) 4-MeC6H4 (5b) 8b 91
3 H/Me (1a) 4-ClC6H4 (5c) 8c 90
4 H/Me (1a) Ph (5d) 8d 89
5 H/Me (1a) 4-NO2C6H4 (5e) 8e 71
6 H/Me (1a) 2,4-2ClC6H3 (5f) 8f 72
7 H/t-Bu (1b) 4-MeOC6H4 (5a) 8g 89
8 H/Bn (1c) 4-MeOC6H4 (5a) 8h 88
9 Me/Me (1d) 4-MeOC6H4 (5a) 8i 74
10 Me/Me (1d) 4-ClC6H4 (5c) 8j 66
11 Me/Bn (1e) 4-MeOC6H4 (5a) 8k 69
12 Et/Bn (1f) 4-MeOC6H4 (5a) 81 48
a

Reactions were carried out on a 0.5 mmol scale: 1 (0.6 mmol), 5 (0.5 mmol), 4 Å MS (100 mg), in 3.0 mL DCM with Rh2(OAc)4 (2.0 mol%) at room temperature; then Sc(OTf)3 (5.0 mol%) was added and stirred at room temperature overnight.

b

Isolated yield of 8 based on limiting reagent 5.