Direct synthesis of α-hydroxyketone phosphates from terminal alkynes and H-phosphine oxides in the presence of PhI(OAc)2 and H2O

Hu, Dongyan; Li, Meng‐Shun; Zhong, Wen‐De; Ji, Jian‐Xin; Zhu, Jin; Wei, Wei; Zhang, Qiang; Cheng, Ming

doi:10.1016/j.cclet.2016.05.029

Cited by 7 publications

(2 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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. [31] The reaction was tolerant to a variety of aryl-and alkyl-substituted acetylenes, as well as different arene moieties on the phosphine oxide (not shown), and demonstrated the same regiospecificity. The authors proposed the reaction to occur via in situ generation of a phosphoryloxy iodane, which then engages the alkyne in a manner analogous to 2 or 65-67 (see Scheme 10).…”

Section: 2c Oxyphosphorylation Of Terminal Acetylenesmentioning

confidence: 90%

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

Section: 2c Oxyphosphorylation Of Terminal Acetylenesmentioning

confidence: 90%

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

2018

View full text Add to dashboard Cite

show abstract

“…Along this line, Zhang, and Cheng reported a unique and efficient protocol for the metal-free direct synthesis of diaryl (2-oxo-2-alkyl/arylethyl)phosphinates from terminal alkynes, H-phosphine oxides, and water. 33 Careful screening of a number of common oxidants such as H 2 O 2 , TBHP, PhI(OAc) 2 , K 2 S 2 O 8 , and m -CPBA; led to PhI(OAc) 2 as the most suitable oxidant for this transformation and among the various organic solvents like THF, DCE, EtOH, DMF, MeCN, 1,4-dioxane, and toluene; MeCN proved to be the most efficient solvent. Both aromatic and aliphatic alkynes 44 and a variety of electron-rich and electron-deficient symmetrical diaryl H-phosphine oxides 45 easily took part in the reaction under optimized reaction conditions and provided the desired diaryl (2-oxo-2-alkyl/arylethyl)phosphinates 46 in good to excellent yields within 24 h ( Scheme 17 ).…”

Section: Oxyphosphorylation Of Alkynesmentioning

confidence: 99%