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. 2021 Jun 11;23(13):5024–5027. doi: 10.1021/acs.orglett.1c01530

Table 1. Comparison of Sulfonyl Hypoiodites with Other Known Electrophilic Iodinating Methodsa.

graphic file with name ol1c01530_0002.jpg

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%
a

Reactions were carried out on a 0.1 mmol scale.

b

Yields determined by 1H NMR spectroscopy with dibromomethane as an internal standard.