Reductive Bromination Research Articles

Reductive bromination of N, N-bis(4-tert-butylphenyl)hydroxylamine

Unlike most arenes, N, N-bis(4-tert-butylphenyl)hydroxylamine reacts with Br2via the reductive bromination mechanism. Here, two hydrogens in ortho positions of benzene rings are substituted by Br2 and provide two-electron reduction of hydroxylamine to amine.

ChemInform Abstract: Indium(III)‐Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One‐Pot Transformation to Alkyl Halides and Amine Derivatives.

Highly effective indium(III)-catalyzed reductive bromination or iodination of a variety of carboxylic acids with 1,1,3,3-tetramethyldisiloxane (TMDS) and a source of bromine or iodine is described. This functional group interconversion has high tolerance for several functional groups, such as halogens, a hydroxy group, a nitro group, an olefin part, and a sulfide moiety. This indium catalytic system is also applicable to the reductive iodination of aldehyded, acyl chlorides, and esters. Furthermore, this reducing system can be applied to the one-pot synthesis of alkyl halides and amine derivatives via the addition of nucleophiles. Insight into the reaction mechanism was gained via the time course of 1H and 13C NMR monitoring experiments and the corresponding stepwise reactions.

Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives

Highly effective indium(III)-catalyzed reductive bromination or iodination of a variety of carboxylic acids with 1,1,3,3-tetramethyldisiloxane (TMDS) and a source of bromine or iodine is described. This functional group interconversion has high tolerance for several functional groups, such as halogens, a hydroxy group, a nitro group, an olefin part, and a sulfide moiety. This indium catalytic system is also applicable to the reductive iodination of aldehyded, acyl chlorides, and esters. Furthermore, this reducing system can be applied to the one-pot synthesis of alkyl halides and amine derivatives via the addition of nucleophiles. Insight into the reaction mechanism was gained via the time course of (1)H and (13)C NMR monitoring experiments and the corresponding stepwise reactions.

Oxidation and reductive bromination of Bis(4-tert-butylphenyl)aminoxyl

One-electron oxidation of bis(4-tert-butylphenyl)aminoxyl with antimony pentachloride and bromine leads to the formation of oxoammonium salts with anions SbCl6− and Br3− respectively. The salt with the Br3− anion converted at heating into a mixture of bromodiphenylamines which formed also from the aminoxyl as a result of previously unknown reaction of three-electron reductive bromination. The mechanisms of these reactions were assumed.

ChemInform Abstract: Indium‐Catalyzed Reductive Bromination of Carboxylic Acids Leading to Alkyl Bromides.

AbstractThe reducing system is selective for carboxylic acids and other functional groups are not attacked.

From Carboxylic Acids to Alkyl Bromides by Reductive Bromination

From Carboxylic Acids to Alkyl Bromides by Reductive Bromination

Indium-Catalyzed Reductive Bromination of Carboxylic Acids Leading to Alkyl Bromides

The combination of 1,1,3,3-tetramethyldisiloxane (TMDS) and trimethylbromosilane (Me(3)SiBr) with a catalytic amount of indium bromide (InBr(3)) undertook direct bromination of carboxylic acids, which produced the corresponding alkyl bromides in good to excellent yields. The reducing system was tolerant to several functional groups.

An efficient synthesis of benzyl bromides from aromatic aldehydes using polymethylhydrosiloxane and (bromodimethyl)sulfonium bromide or N-bromosuccinimide

Polymethylhydrosiloxane (PMHS) in combination with (bromodimethyl)sulfonium bromide or NBS has been utilized for the first time for reductive bromination of aromatic aldehydes at room temperature to afford the corresponding benzyl bromides in excellent yields.

Palladium‐Catalyzed Selective Amination of Haloaromatics on KF‐Alumina Surface.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Palladium-Catalyzed Selective Amination of Haloaromatics on KF-Alumina Surface

An efficient palladium-catalyzed amination, including polyaminations of aromatic bromides mediated on a surface of KF-alumina, is reported. The solvent-free one-pot protocol avoids the use of a strong base (sodium tert-butoxide) making it applicable to substrates containing a base-sensitive functional group. It proceeds without concomitant reductive bromination and provides access to selective amination of polyhaloaromatics.

ChemInform Abstract: A Novel Silylcopper Catalyst for the Reductive Bromination of Hajos Dione. Improved Preparation of a CD Synthon for the Synthesis of Vitamin D.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A novel silylcopper catalyst for the reductive bromination of Hajos dione. Improved preparation of a CD synthon for the synthesis of vitamin D.

ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTA Novel Silylcopper Catalyst for the Reductive Bromination of Hajos Dione. Improved Preparation of a CD Synthon for the Synthesis of Vitamin DAndrzej R. Daniewski and Wen LiuView Author Information Chemical Synthesis − Process Research, Non-Clinical Development, Pre-Clinical Research and Development, Hoffmann-La Roche, Inc., Nutley, New Jersey 07110 [email protected]Cite this: J. Org. Chem. 2001, 66, 2, 626–628Publication Date (Web):December 30, 2000Publication History Received5 October 2000Published online30 December 2000Published inissue 1 January 2001https://doi.org/10.1021/jo0014414Copyright © 2001 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1597Altmetric-Citations27LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (47 KB) Get e-AlertsSUBJECTS:Anions,Catalysts,Copper,Halogenation,Mixtures Get e-Alerts

Reductive bromination of aromatic aldehydes using alkylboron dibromides

The reductive bromination of aromatic aldehydes with isopinocampheyl boron dibromide in hexane at room temperature produces the corresponding benzyl bromides in excellent yields.

ChemInform Abstract: Trimethylamine‐Bromoborane as Alternative Reagent for Reductive Bromination of Aromatic Carbonyl Compounds.

ChemInform Abstract: Trimethylamine‐Bromoborane as Alternative Reagent for Reductive Bromination of Aromatic Carbonyl Compounds.

Studies in the Thianthrene System: Bromination and Reductive Bromination

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStudies in the Thianthrene System: Bromination and Reductive BrominationHenry Gilman and Dhairyasheel R. SwayampatiCite this: J. Am. Chem. Soc. 1955, 77, 22, 5944–5948Publication Date (Print):November 1, 1955Publication History Published online1 May 2002Published inissue 1 November 1955https://doi.org/10.1021/ja01627a049RIGHTS & PERMISSIONSArticle Views408Altmetric-Citations21LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (658 KB) Get e-Alerts Get e-Alerts