ABSTRACT
The stereospecific, substrate (nitrogen source)-controlled intermolecular anti- and syn-1,2-diaminations of unactivated alkenes using the same catalysis (an iodine catalyst) is reported. The combined use of the two potential methods provides access to all of the disastereomeric forms of 1,2-diamines in spite of the availability of E- and Z-alkenes, and the resulting products can be readily converted into free vicinal diamines.
ABSTRACT
An oxidative amination of allenes using a single hypervalent iodine reagent is reported. The reaction proceeds very efficiently for monosubstituted allenes and leads to formation of the corresponding propargylic amines, either as the internal or as the terminal amine. The respective reaction outcome could be influenced in favor of the former product by addition of triphenylphosphine oxide to the iodine(III) reagent.
ABSTRACT
A straightforward synthetic method of both symmetric and unsymmetric aromatic azo compounds through an efficient and cross-selective oxidative dimerization of aromatic amines using tert-butyl hypoiodite (t-BuOI) under metal-free and mild conditions has been developed. This method was also found applicable to the synthesis of heteroaromatic azo compounds. The spectroscopic study indicates the involvement of N,N-diiodoanilines in the oxidative reaction as the key intermediate.
ABSTRACT
Hypervalent iodine(III)-induced oxidative [4+2] annulation of o-phenylenediamines and electron-deficient alkynes under metal-free conditions has been developed. The reaction allows for direct access to quinoxalines bearing two electron-withdrawing groups in an efficient manner.
Subject(s)
Alkynes/chemistry , Iodine/chemistry , Phenylenediamines/chemistry , Quinoxalines/chemistry , Cycloaddition Reaction , Electrons , Metals/chemistry , Oxidation-ReductionABSTRACT
A cyclizative atmospheric CO(2) fixation by unsaturated amines such as allyl and propargyl amines under mild reaction conditions, efficiently leading to cyclic carbamates bearing a iodomethyl group, have been developed utilizing tert-butyl hypoiodite (t-BuOI).
ABSTRACT
It's all the hype: An oxidative dimerization reaction of aromatic amines utilizing tert-butyl hypoiodite (tBuOI) under mild reaction conditions leads to aromatic azo compounds. The method allows access to unsymmetric aromatic azo compounds, which are difficult to prepare by conventional synthetic methods, in a selective manner.
Subject(s)
Amines/chemistry , Azo Compounds/chemical synthesis , Butanes/chemistry , Azo Compounds/chemistry , Dimerization , Molecular Structure , Oxidation-Reduction , StereoisomerismABSTRACT
tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.