Table 1. Comparison of Sulfonyl Hypoiodites with Other Known Electrophilic Iodinating Methodsa.
comparison with electrophilic iodinating methods | yieldb |
---|---|
(MsO)2 (1, 1.8 equiv) + TBAI (2.0 equiv) in 0.2 M MeCN | 84% |
I2 (1.3 equiv) + AgOMs (1.3 equiv) in 0.2 M MeCN | 90% |
I2 (1 equiv) + AgOTf (1 equiv) in 0.2 M DCM | 18% |
NIS (1 equiv) in 0.2 M HFIP | 54% |
NIS (10 equiv) in 0.2 M TfOH | 0% |
Ph2S2 (5 mol %) + DIH (0.75 equiv) in 0.3 M MeCN | 29% |
I2 (1 equiv) + AgPF6 (1 equiv) in 0.2 M DCM | 16% |
Reactions were carried out on a 0.1 mmol scale.
Yields determined by 1H NMR spectroscopy with dibromomethane as an internal standard.