The N-amination of heterocyclic compounds 1a-k with O-benzoylhydroxylamine derivatives 5 was developed and demonstrated to be a superior alternative to existing N-amination methods. A structure-reactivity relationship study was performed on variously substituted O-benzoylhydroxylamine derivatives, leading to the discovery of the novel and more efficient aminating reagents 5h and 5i.
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Pd-Catalyzed Alkene Diamination Reactions with -Benzoylhydroxylamine Electrophiles: Evidence Supporting a Pd(II/IV) Catalytic Cycle, the Role of 2,4-Pentanedione Derivatives as Ligands, and Expanded Substrate Scope.
J Org Chem
September 2021
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, Michigan 48109-1055, United States.
This article describes continued studies on Pd-catalyzed alkene diamination reactions between -allylguanidines or ureas and -benzoylhydroxylamine derivatives, which serve as N-centered electrophiles. The transformations generate cyclic guanidines and ureas bearing dialkylaminomethyl groups in moderate to good yield. We describe new mechanistic experiments that have led to a revised mechanistic hypothesis that involves a key oxidative addition of the electrophile to a Pd complex, followed by reductive elimination from Pd to form the alkyl carbon-nitrogen bond.
View Article and Find Full Text PDFPd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups.
Org Lett
June 2018
Department of Chemistry , University of Michigan , 930 North University Avenue, Ann Arbor , Michigan 48109-1055 , United States.
The Pd-catalyzed coupling of N-allylguanidines or N-allylureas with O-benzoylhydroxylamine derivatives affords cyclic guanidines or cyclic ureas bearing dialkylaminomethyl groups. The desired products are obtained in good yield, and substrates bearing substituents at the allylic position are transformed with moderate diastereoselectivity. The mechanism of these reactions appears to involve anti-aminopalladation of the alkene, followed by a rare spC-spN bond-forming reductive elimination from an alkylpalladium complex that contains β-hydrogen atoms.
View Article and Find Full Text PDFCopper-Catalyzed Amino Lactonization and Amino Oxygenation of Alkenes Using O-Benzoylhydroxylamines.
J Am Chem Soc
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Department of Chemistry, Duke University, Durham, North Carolina 27708, United States.
A copper-catalyzed amino lactonization of unsaturated carboxylic acids has been achieved as well as the analogous intermolecular three-component amino oxygenation of olefins. The transformation features mild conditions and a remarkably broad substrate scope, offering a novel and efficient approach to construct a wide range of amino lactones as well as 1,2-amino alcohol derivatives. Mechanistic studies suggest that the reaction proceeds via a distinctive O-benzoylhydroxylamine-promoted electrophilic amination of alkenes.
View Article and Find Full Text PDFIron-catalyzed intermolecular hydroamination of styrenes.
Org Lett
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Department of Chemistry, Texas A&M University , College Station, Texas 77843-3255, United States.
An iron-catalyzed formal hydroamination of alkenes has been developed. It features O-benzoyl-N,N-dialkylhydroxylamines as the electrophilic nitrogen source and cyclopentylmagnesium bromide as the reducing agent for intermolecular hydroamination of styrene and derivatives with good yield and excellent Markovnikov regioselectivity. The reaction presumably proceeds through the iron-catalyzed hydrometalation of styrene followed by electrophilic amination with the electrophilic O-benzoylhydroxylamine.
View Article and Find Full Text PDFAmination of heterocyclic compounds with o-benzoylhydroxylamine derivatives.
Org Lett
September 2007
Department of Process Research and Development and Drug Discovery Chemistry, Bristol-Myers Squibb Research & Development, PO Box 4000, Princeton, New Jersey 08543, USA.
The N-amination of heterocyclic compounds 1a-k with O-benzoylhydroxylamine derivatives 5 was developed and demonstrated to be a superior alternative to existing N-amination methods. A structure-reactivity relationship study was performed on variously substituted O-benzoylhydroxylamine derivatives, leading to the discovery of the novel and more efficient aminating reagents 5h and 5i.
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