New Organohypervalent Iodine Reagents for α-Methylphosphonylations and α-Diphenyl- and α-Dimethylphosphinylations

Moriarty, Robert M.; Condeiu, C.; Tao, Anping; Prakash, Om

doi:10.1016/s0040-4039(97)00388-2

Cited by 29 publications

(16 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The proposed mechanism for the α-phosphoryloxylaction of ketones is similar to the literature procedure [21], which is shown as follows (Scheme 3).…”

Section: Resultsmentioning

confidence: 70%

An Efficient α-Phosphoryloxylation of Ketones

Pu¹,

Yan²

2011

IJOC

View full text Add to dashboard Cite

show abstract

“…The proposed mechanism for the α-phosphoryloxylaction of ketones is similar to the literature procedure [21], which is shown as follows (Scheme 3).…”

Section: Resultsmentioning

confidence: 70%

An Efficient α-Phosphoryloxylation of Ketones

Pu¹,

Yan²

2011

IJOC

View full text Add to dashboard Cite

show abstract

“…[10] Moriarty and Prakash subsequently demonstrated that the analogous derivatives 5-7 could also be prepared by the reaction of various phosphonic and phosphinic acids with iodosobenzene (4, Scheme 2 b). [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).…”

Section: Synthesis Of Phosphorus-containing Hvi Reagentsmentioning

confidence: 99%

“…Treating the iodanes with an equimolar amount of ketones (acetophenone or cyclohexanone) or b-dicarbonyls (methyl acetoacetate or dibenzoylmethane) gave the corresponding products 68-71 in up to 47 % yield (Scheme 10). [11] The reactions using 65 and 66 were generally lower yielding than those with 67, which the authors attributed to the relative instability of the resulting phosphinate products.…”

Section: 2a A-oxyphosphorylation Of Carbonyl Compoundsmentioning

confidence: 99%

“…60, 79-81) in a 17-42 % yield (Scheme 14 a). [30] In 1997, Moriarty showed this strategy was also possible for preparing a-carbonyl phosphonato and phosphinato compounds 68, 82 and 83 from phenylacetylene (Scheme 14 b); [11] however, the yields were not as high as when prepared via ketone a-oxyphosphorylation (see Scheme 9). In 2016, an improved method for the synthesis of a-ketol phosphinates from terminal alkynes was advanced by treating a phosphine oxide with (diacetoxyiodo)benzene 1 in wet CH 3 CN to afford 82, 84-86 in 68-90 % yield.…”

Section: 2c Oxyphosphorylation Of Terminal Acetylenesmentioning

confidence: 99%

See 1 more Smart Citation

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

2018

View full text Add to dashboard Cite

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.

show abstract

“…[67] Moriarty prepared similar reagents for the α-methylphosphonylation of ketones, as well as for α-diphenyl and α-dimethylphosphinylation reactions. [68] Liang and co-workers used IBX in the presence of potassium iodide in order to prepare a range of α-(2-iodobenzoyloxy)ketones (Scheme 29). Moriarty used iodosylbenzene in conjunction with boron trifluoride etherate to perform a range of different α-functionalizations of β-diketones and β-ketoesters, including α-mesyloxylation and alkoxylation.…”

Section: Other α-Oxygenationsmentioning

confidence: 99%