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

被引:20
作者
Murphy, Graham K. [1 ]
Racicot, Lanne [1 ,2 ]
Carle, Myriam S. [1 ]
机构
[1] Univ Waterloo, Dept Chem, 200 Univ Ave W, Waterloo, ON N2L 3G1, Canada
[2] McMaster Univ, Dept Chem & Chem Biol, Hamilton, ON L8S 4L8, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
halogenation; hypervalent compounds; iodine; organophosphorus; phosphorylation; SECONDARY PHOSPHINE OXIDES; DIARYLIODONIUM SALTS; ELECTROPHILIC TRIFLUOROMETHYLATION; ALPHA-PHOSPHORYLOXYLATION; PHOSPHORUS NUCLEOPHILES; POLYVALENT IODINE; DIRECT CONVERSION; ALKYNYLPHENYLIODONIUM TOSYLATES; DIALKYL ALKYNYLPHOSPHONATES; FUNCTIONALIZED PHOSPHONIUM;
D O I
10.1002/ajoc.201800058
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
引用
收藏
页码:837 / 851
页数:15
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