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455 results on '"Doye, Sven"'

2. Catalytic C–H Functionalization of Trimethylamine.

Author

Geik, Dennis, Büker, Alina, Fornfeist, Felix, Schmidtmann, Marc, and Doye, Sven

Subjects
TRIMETHYLAMINE, CHEMICAL processes, ORGANIC chemistry, METHYL vinyl ketone, INDUSTRIAL chemistry, TRIMETHYLAMINE oxide
Abstract

This article explores the catalytic C–H functionalization of trimethylamine, an important intermediate in the chemical industry. Trimethylamine is often obtained as an undesired by-product, and separating it from other methylamines is challenging and expensive. The authors discuss the development of new chemical reactions that use trimethylamine as a starting material for the synthesis of valuable products, particularly those with a dimethylaminomethyl substructure commonly found in pharmaceuticals. The article reports successful reactions of trimethylamine with various compounds, offering flexible and direct methods for its functionalization. The authors highlight the efficient activation of the α-C–H bond of trimethylamine using titanium catalysts, which allows for the synthesis of various dimethylaminomethyl-substituted products. The article also mentions the successful synthesis of the antidepressant butriptyline as an example of the potential of these new reactions. The assistance of Jessica Reimer and the supply of ampoules by Kirstin Glaser, Karin Grittner, and Frank Fleischer are acknowledged. [Extracted from the article]

Published
2024
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5. Titanium-Catalyzed Intermolecular Hydroaminoalkylation of Terminal Alkynes.

Author

Thye, Hermann, Fornfeist, Felix, Geik, Dennis, Schlüschen, Levi L., Schmidtmann, Marc, and Doye, Sven

Subjects
TERTIARY amines, ALKYNES, SCIENTIFIC literature, BIOACTIVE compounds, TITANIUM catalysts, BENZENE derivatives, TOLUENE
Abstract

(E)- N -(2-Cyclohexyl-1-phenyl-3-(trimethylsilyl)allyl)aniline (19) General procedure A was used to react I N i -benzylaniline (183 mg, 1.0 mmol) with (cyclohexylethynyl)trimethylsilane (180 mg, 1.0 mmol) in the presence of catalyst B II-Bu b (111 mg, 0.1 mmol) for 24 h at 140 °C. Keywords: alkynes; allylamines; C-H activation; hydroaminoalkyl-ation; titanium; catalysis EN alkynes allylamines C-H activation hydroaminoalkyl-ation titanium catalysis 3759 3776 18 11/01/23 20231116 NES 231116 Graph The catalytic hydroaminoalkylation of alkenes [1][8] (Scheme 1), which takes place by a 100% atom-economical addition of the -C-H bond of a primary, [8] secondary, [8][8][8][8] or tertiary [8][8] amine across the alkene double bond, has received considerable attention over the past 15 years. N -(3,3-Dimethyl-2-methylenebutyl)aniline (1) 4d General procedure A was used to react I N i -methylaniline (107 mg, 1.0 mmol) with I tert i -butylacetylene (99 mg, 1.2 mmol) in the presence of catalyst B II-DIPP b (194 mg, 0.1 mmol) for 24 h at 140 °C. 3-Chloro- N -(3,3-dimethyl-2-methylenebutyl)aniline (5) General procedure A was used to react 3-chloro- I N i -methylaniline (142 mg, 1.0 mmol) with I tert i -butylacetylene (99 mg, 1.2 mmol) in the presence of catalyst B II-DIPP b (194 mg, 0.1 mmol) for 24 h at 140 °C. N -(3,3-Dimethyl-2-methylenebutyl)-4-(trifluoromethoxy)aniline (7) General procedure A was used to react I N i -methyl-4-(trifluoromethoxy)aniline (191 mg, 1.0 mmol) with I tert i -butylacetylene (99 mg, 1.2 mmol) in the presence of catalyst B II-DIPP b (194 mg, 0.1 mmol) for 24 h at 140 °C. [Extracted from the article]

Published
2023
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12. Cp*(sub)2TiMe(sub)2: an improved catalyst for the intermolecular addition of n-alkyl- and benzylamines to alkynes

Author

Heutling, Andreas and Doye, Sven

Subjects
Olefins -- Research, Chemical reactions -- Analysis, Catalysts -- Analysis, Organic compounds -- Synthesis, Biological sciences, Chemistry
Abstract

Results demonstrate that Cp*(sub)2TiMe(sub)2 is an excellent catalyst for intramolecular addition of n-alkyl- and benzylamines to internal alkynes. Data show that at 2.0-6.0 percent mol of the catalyst, hydroamination reaction between n-propyl-, n-hexyl-, benzyl-, p-methoxybenzyl and diphenylacetylene, 3-hexyne or 4-octyne is completed within 24 hours at 114 C.

Published
2002

27. One-pot procedure for the synthesis of unsymmetrical diarylalkynes

Author

Severin, Rene, Reimer, Jessica, and Doye, Sven

Subjects
Acetylene -- Chemical properties, Arylation -- Analysis, Copper -- Chemical properties, Hydroxides -- Chemical properties, Palladium catalysts -- Chemical properties, Biological sciences, Chemistry
Abstract

Unsymmetrical diarylalkynes are obtained by a one-pot procedure from two different aryl halides and (trimethylsilyl)acetylene. After desilylation of the aryl(trimethylsilyl)acetylene with aqueous potassium hydroxide, a second Sonogashira coupling with an aryl iodide that does not need any additional Pd/Cu-catalyst has given access to an unsymmetrical diarylalkyne.

Published
2010

40. Thieme Chemistry Journals Awardees – Where Are They Now? Titanium-Catalyzed Hydroaminoalkylation of Vinylsilanes and a One-Pot Procedure for the Synthesis of 1,4-Benzoazasilines.

Author

Lühning, Lars H., Rosien, Michael, and Doye, Sven

Subjects
TITANIUM catalysts, ALKYLATION, ALKENE synthesis
Abstract

Vinylsilanes undergo intermolecular alkene hydroaminoalkylation with secondary amines in the presence of a titanium mono( aminopyridinato) catalyst to give the branched hydroaminoalkylation products with high regioselectivity. Corresponding reactions of a suitable (2-bromophenyl)vinylsilane combined with a subsequent intramolecular Buchwald–Hartwig amination result in the development of an elegant one-pot procedure for the synthesis of 1,4-benzoazasilines. [ABSTRACT FROM AUTHOR]

Published
2017
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49. A general copper-catalyzed synthesis of diaryl ethers

Author

Marcoux, Jean-Francois, Doye, Sven, and Buchwald, Stephen L.

Subjects
Ethers -- Research, Copper -- Usage, Aromatic compounds -- Research, Chemistry
Abstract

A general process for the preparation of diaryl ethers from the reaction of aryl bromides and iodides with a variety of phenols is presented. The new process employs a catalytic quantity of a copper complex, cesium carbonate as base, and does not require the formation of phenoxide anion before the reaction. It is also able to use a nonpolar solvent, lower reaction temperatures, and a stoichiometric quantity of a carboxylic acid in the reactions of unactivated aryl halides.

Published
1997

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