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. Author manuscript; available in PMC: 2009 Jul 22.
Published in final edited form as: Tetrahedron Lett. 2007 Jun 4;48(23):4047–4050. doi: 10.1016/j.tetlet.2007.04.021

Table 4.

Triflic acid catalyzed synthesis of N-sulfonyl carbazoles from aryl sulfonamides and 2,5-dimethoxytetrahydrofuran.a

graphic file with name nihms23907f6.jpg
Entry Ar Time
(h)
Selectivityb
(%)
Yieldc
(%)
1 C6H5 2 92 79
2 p-CH3C6H4 2 91 81
3 p-OCH3C6H4 2 88 75
4 p-BrC6H4 2 85 77
5 o-CH3C6H4 2 91 82
6 p-ClC6H4 2 93 86
7 p-NO2C6H4 2 85 75
8 Naphth-2-yl 2 91 82
a

Reaction conditions: sulfonamide (0.636 mmol), 2,5-dimethoxytetrahydrofuran (5 eqv.), TfOH (3.5 eqv.), RT, 2h.

b

Determined by GCMS.

c

Isolated yields after flash chromatography.