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1.
Org Biomol Chem ; 20(34): 6750-6754, 2022 08 31.
Article in English | MEDLINE | ID: mdl-35938985

ABSTRACT

An original and facile method for the generation of ß-naphtha-1-thioquinones using DAST and 2-naphthols has been developed. A series of dehydro-2-naphthol-1-sulphides or naphtha-oxathiane derivatives were synthesized by in situ Diels-Alder cycloaddition reactions of ß-naphtha-1-thioquinone with itself or various alkenes.


Subject(s)
Naphthols , Alkanes , Cycloaddition Reaction , Diethylamines , Fluorine , Solvents , Stereoisomerism
2.
Org Biomol Chem ; 18(9): 1738-1742, 2020 03 04.
Article in English | MEDLINE | ID: mdl-32077880

ABSTRACT

A novel and efficient method for the generation of alkyl radicals and the alkylation of quinoline and pyridine derivatives under mild conditions has been developed. This strategy allows the direct alkylation of heteroaromatics in the absence of an external oxidant. A preliminary mechanistic study suggests that the present reaction probably proceeds via an intermolecular HAT process.

3.
J Org Chem ; 84(7): 4040-4049, 2019 04 05.
Article in English | MEDLINE | ID: mdl-30854850

ABSTRACT

A novel oxidation of benzylic C-H bonds for the synthesis of diverse six-membered N-heteroaromatic aldehydes and ketones has been developed. The obvious advantages of this approach are the simple operation, mild reaction conditions, and without use of toxic reagent and transition metal. The present method should provide a useful access for the synthesis and modification of N-heterocycles.

4.
Org Lett ; 20(13): 3732-3735, 2018 07 06.
Article in English | MEDLINE | ID: mdl-29920105

ABSTRACT

An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.

5.
J Org Chem ; 82(16): 8604-8610, 2017 08 18.
Article in English | MEDLINE | ID: mdl-28704047

ABSTRACT

An efficient CuI-catalyzed fluorodesulfurization for the synthesis of monofluoromethyl aryl ethers using DAST at room temperature has been developed. This approach exhibits a good functional group tolerance, a broad substrate scope, and a high synthesis efficiency.

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