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US 10,494,328 B2Granted
Amination and hydroxylation of arylmetal compounds
AssigneeWilliam Marsh Rice University
InventorsHongyin Gao, Zhe Zhou, Laszlo Kurti
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Abstract
In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.
Claims16
A method of preparing an aminoaromatic compound or a hydroxyaromatic compound comprising:
- (A) admixing a metal aromatic compound with an oxaziridine compound to form a first reaction mixture under conditions sufficient to cause a reaction to obtain an anionic intermediate;
- wherein the oxaziridine compound is further defined as:
- wherein:
- R1 and R1′ are each independently alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤12), or a substituted version of any of these groups, or R1 and R1′ are taken together and are a cycloalkanediyl(C≤18) or substituted cycloalkanediyl(C≤18);
- and
- R2 is hydrogen or alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), or a substituted version of any of these three groups;
- (B) admixing a weak acid with the anionic intermediate to obtain a second reaction mixture under conditions sufficient to obtain an aminoaromatic compound or a hydroxyaromatic compound.
4 more elements
A method of preparing an aminoaromatic compound comprising:
- (A) admixing a metal aromatic compound with
- an oxaziridine compound
- in presence of a copper reagent to form a first reaction mixture under conditions sufficient to cause a reaction to obtain an anionic intermediate;
- wherein the oxaziridine compound is further defined as:
- wherein:
- R1 and R1′ are each independently alkyl(C≤12), cycloalkyl(C≤12), aryl(C≤12), or a substituted version of any of these groups, or R1 and R1′ are taken together and are a cycloalkanediyl(C≤18) or substituted cycloalkanediyl(C≤18);
- and
- R2 is hydrogen or alkyl(C≤12), aryl(C≤12), aralkyl(C≤12), or a substituted version of any of these three groups;
- (B) admixing a weak acid with the anionic intermediate to obtain a second reaction mixture under conditions sufficient to obtain an aminoaromatic compound.
6 more elements
Dependencies are inferred from the claim text.