Convenient, Solvent-Free Method for Preparation of [Hydroxy(phosphoryloxy)iodo]arenes

Zhu, Min; Cai, Cheng Gang; Wei, Ke; Shao, Jing

doi:10.1080/00397910903097229

Cited by 3 publications

(1 citation statement)

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“…[11] In 2010, Zhu and co-workers published a solvent-free approach to iodanes 2 and 3, rapidly achieved by grinding 1 and the dialkylphosphates (Scheme 2 c). [12] The benziodoxolone-derived analog 9 was also reported, being prepared from chlorobenziodoxolone 8 and silver diphenyl phosphate (Scheme 2 d). [13][14][15] Hypervalent iodine reagents possessing intramolecular phosphorus-based stabilizing groups are also known.…”

Section: Synthesis Of Phosphorus-containing Hvi Reagentsmentioning

confidence: 99%

The Chemistry between Hypervalent Iodine(III) Reagents and Organophosphorus Compounds

2018

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The intersection between the chemistries of hypervalent iodine (HVI) reagents and organophosphorus compounds holds significant potential. To date, the merging of these research spheres has led to novel iodane motifs, many of which have been used in new oxyphosphorylation methodologies. In addition, HVI reagents have proven easily capable of transferring electrophilic carbon-based (alkyl, aryl, al-kynyl, etc.) ligands to various phosphorus nucleophiles. Furthermore, the ease with which HVI reagents oxidize phosphorus has led to novel esterification, amidation, alcohol functionalization and peptide coupling reactions. This Focus Review summarizes the chemistry to-date between these two important classes of compounds. Scheme 1. General reactivity modes of l 3 -iodanes.[a] Dr.Scheme 2. Phosphorus-containing HVI reagents.Scheme 3. ortho-Stabilized HVI reagents. Scheme 4. Phosphorus-containing HVI reagents generated in situ. Scheme 5. Synthesis of alkynyl phosphate esters. Scheme 6. Oxyphosphorylation of vinyliodonium salts. Scheme 10. Synthesis of a-carbonyl phosphonates and phosphinates. Scheme 11. Synthesis of a-carbonyl phosphonates. Scheme 12. Synthesis of a-carbonyl phosphonates via in situ-generated 26. Scheme 13. Synthesis of tris-ketol phosphates. Scheme 19. Phosphorylation of silylenol ethers. Scheme 20. Preparation of phosphonates by arylation of phosphites. Scheme 21. Arylation of PÀH phosphine oxides and phosphonates. Scheme 22. Synthesis of bis(triphenylphosphonium) salts. Scheme 23. Phosphorylation of alkynyliodonium salts with phosphites. Scheme 28. Synthesis of vinyl phosphonates from vinyl iodonium salts. Scheme 30. Trifluoromethylation of naphthyl-derived phosphines. Scheme 29. Trifluoromethylation of phosphines. Scheme 35. Peptide coupling mediated by PPh 3 and 200 or 217.Scheme 36. Synthesis of acyl and alkyl chlorides, and alkyl fluorides using 207 and 208 generated in situ.Scheme 37. Synthesis of mixed iodonium phosphonium ylides.

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