Hypervalent Iodine Iodinative Decarboxylation Of Cubyl And Homocubyl Carboxylic Acids

1988 ◽  
Author(s):  
Robert M. Moriarty ◽  
Jaffar S. Khosrowshahi ◽  
Tomasz Dalecki
Keyword(s):  
Carboxylic Acids ◽  
Hypervalent Iodine

Synthesis of O-Aroyl-N,N-dimethylhydroxylamines through Hypervalent Iodine-Mediated Amination of Carboxylic Acids with N,N-Dimethylformamide

Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4303-4308 ◽  
Author(s):  
Dong Li ◽  
Chuancheng Zhang ◽  
Qiang Yue ◽  
Zhen Xiao ◽  
Xianglan Wang ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Functional Group ◽  
Hypervalent Iodine ◽  
Electrophilic Amination ◽  
Mild Conditions

An efficient protocol for the synthesis of O-aroyl-N,N-dimethylhydroxylamines, which are important electrophilic amination reagents, is described. The reaction between carboxylic acids and N,N-dimethylformamide is mediated by hypervalent iodine and occurs under mild conditions at room temperature to give the desired products in good yields. The process shows good functional group compatibility and air and moisture tolerance.

Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones

Synthesis ◽  
2017 ◽  
Vol 49 (13) ◽  
pp. 2907-2912 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Satoshi Minakata ◽  
Kenta Takemoto ◽  
Shunsuke Yahata ◽  
Takumi Kojima
Keyword(s):  
Organic Chemistry ◽  
Carboxylic Acids ◽  
Present Method ◽  
Medicinal Chemistry ◽  
Oxidative Cyclization ◽  
Hypervalent Iodine ◽  
Efficient Synthesis ◽  
Substitution Pattern ◽  
Unsaturated Carboxylic Acids

The oxidative cyclization of β-substituted β,γ-unsaturated carboxylic acids using a hypervalent iodine reagent to provide 4-substituted furan-2-one products, is reported. In this cyclization, the use of a highly electrophilic PhI(OTf)2, which is in situ prepared from PhI(OAc)2 and Me3SiOTf, is crucial. Depending on the substitution pattern at the α-position of the substrates, furan-2(5H)-ones or furan-2(3H)-ones are produced. Thus, the present method offers a useful tool for accessing various types of 4-substituted furan-2-ones that are important structural motifs in the field of organic chemistry and medicinal chemistry.

ChemInform Abstract: Hypervalent Iodine Iodinative Decarboxylation of Cubyl and Homocubyl Carboxylic Acids.

ChemInform ◽  
1987 ◽  
Vol 18 (44) ◽  
Author(s):  
R. M. MORIARTY ◽  
J. S. KHOSROWSHAHI ◽  
T. M. DALECKI
Keyword(s):  
Carboxylic Acids ◽  
Hypervalent Iodine

A mild method for synthesizing carboxylic acids by oxidation of aldoximes using hypervalent iodine reagents

2018 ◽  
Vol 16 (4) ◽  
pp. 541-544 ◽  
Author(s):  
Akira Nakamura ◽  
Hodaka Kanou ◽  
Junki Tanaka ◽  
Akira Imamiya ◽  
Tomohiro Maegawa ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Hypervalent Iodine

A variety of aldoximes can be efficiently converted into the corresponding carboxylic acids with hypervalent iodine reagent.

scholarly journals Hypervalent iodine(III)-mediated decarboxylative acetoxylation at tertiary and benzylic carbon centers

2018 ◽  
Vol 14 ◽  
pp. 1046-1050 ◽  
Author(s):  
Kensuke Kiyokawa ◽  
Daichi Okumatsu ◽  
Satoshi Minakata
Keyword(s):  
Carboxylic Acids ◽  
Mixed Solvent ◽  
Hypervalent Iodine ◽  
Reaction Conditions ◽  
Carbon Centers ◽  
Benzylic Carbon

The decarboxylative acetoxylation of carboxylic acids using a combination of PhI(OAc)2 and I2 in a CH2Cl2/AcOH mixed solvent is reported. The reaction was successfully applied to two types of carboxylic acids containing an α-quaternary and a benzylic carbon center under mild reaction conditions. The resulting acetates were readily converted into the corresponding alcohols by hydrolysis.

scholarly journals Selective carboxylation of reactive benzylic C–H bonds by a hypervalent iodine(III)/inorganic bromide oxidation system

2018 ◽  
Vol 14 ◽  
pp. 1087-1094 ◽  
Author(s):  
Toshifumi Dohi ◽  
Shohei Ueda ◽  
Kosuke Iwasaki ◽  
Yusuke Tsunoda ◽  
Koji Morimoto ◽  
...  
Keyword(s):  
Organic Solvent ◽  
Carboxylic Acids ◽  
Hypervalent Iodine ◽  
Homolytic Cleavage ◽  
Radical Species ◽  
Direct Introduction ◽  
Mild Conditions ◽  
High Degree ◽  
Oxidation System

An oxidation system comprising phenyliodine(III) diacetate (PIDA) and iodosobenzene with inorganic bromide, i.e., sodium bromide, in an organic solvent led to the direct introduction of carboxylic acids into benzylic C–H bonds under mild conditions. The unique radical species, generated by the homolytic cleavage of the labile I(III)–Br bond of the in situ-formed bromo-λ3-iodane, initiated benzylic carboxylation with a high degree of selectivity for the secondary benzylic position.

Sign in / Sign up

Export Citation Format

Share Document