Beilstein J. Org. Chem.2007,3, No. 19, doi:10.1186/1860-5397-3-19
diiodinated benzyl alcohol 8n in good yield. Oxidation of the alcohol group was not observed.
Based on related iodine(III)-mediated iodinations of arenas [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] we suggest that the hydrated form of 6 oxidizes
iodination reactions.
Conclusion
In conclusion, we disclose that the rarely employed m-iodosylbenzoic acid is an ideal tagged iodine(III) reagent which in our view allows the easiest purification protocol for aryliodine reagents known so far. This tagging concept was utilized in the mild iodination of arenes
but could potentially be applied to most other iodine(III)-mediated reactions.
Hypervalent iodine reagents 1 – 6.
Iodine(III)-promoted iodination of arenes and concept of purification.
Proposed intermediates.
Monoiodination of arenes with m-iodosylbenzoic acid 6 (see Supporting Information File 1 for