Tertiary Allylic Amines Research Articles

Amidopalladation of tertiary allylic amines and of terminal olefins with phthalimide and N-methyltoluenesulfonamide

Amidopalladation of tertiary allylic amines and of terminal olefins with phthalimide and N-methyltoluenesulfonamide

Reaction of tertiary allylic amines with butadiene catalyzed by palladium

Tertiary allylic amines react with butadiene in the presence of palladium(O) with cleavage of the carbon-nitrogen bond of the allylic amine and formation of the unsaturated tertiary amine 4 .

Palladium-catalyzed triethylammonium formate reductions. 4. Reduction of acetylenes to cis-monoenes and hydrogenolysis of tertiary allylic amines

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPalladium-catalyzed triethylammonium formate reductions. 4. Reduction of acetylenes to cis-monoenes and hydrogenolysis of tertiary allylic aminesJohn R. Weir, Babu A. Patel, and Richard F. HeckCite this: J. Org. Chem. 1980, 45, 24, 4926–4931Publication Date (Print):November 1, 1980Publication History Published online1 May 2002Published inissue 1 November 1980https://doi.org/10.1021/jo01312a021RIGHTS & PERMISSIONSArticle Views2352Altmetric-Citations106LEARN 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 (776 KB) Get e-AlertsSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts

Triarylphosphine-Palladium Complexes

Aryl, heterocyclic, benzyl, and vinylic halides undergo facile reactions with carbon monoxide or olefins forming new carbon-carbon bonds under the influence of triarylphosphine-palladium catalysts. The carbon monoxide reactions produce esters in the presence of alcohols, amides in the presence of amines, and aldehydes in the presence of hydrogen. Reactions with olefins produce new olefins in which a vinylic hydrogen is replaced by the organic group from the halide. Some olefins and vinylic halides require the presence of secondary amines to react, in which instance tertiary allylic amines are formed catalytically. Conjugated dienes may be used in place of simple olefins to form products with additional unsaturation. Numerous applications for these reactions in organic synthesis appear likely.

Palladium-catalysed carbonylation of unsaturated compounds

The oxiative carbonylation of olefins in the presence of palladium(II)/copper(II) as catalyst yields β substituted and/or α-β unsaturated carboxylic acid derivatives. The palladium-catalyzed carbonylation of allylic compunds affords β-γ unsaturated carboxylic acid derivatives, while tertiary allylamines can be converted into γ-amino acids. The interaction of confugated and cumulated dienes with π-allylic palladium complexes is described as part of palladium-catalysed synthesis of polyunsaturated carboxylic acid derivatives from a diene, an alcohol and carbon monoxide or from a diene, an allylic compound and carbon monoxide. The kinetics and mechanisms of these reaction are discussed.