Intermolecular hydroaminoalkylation reactions of alkynes with secondary amines, which selectively give access to allylic amines with E configuration of the alkene unit, are achieved in the presence of titanium catalysts. Successful reactions of symmetrically substituted diaryl- and dialkylalkynes as well as a terminal alkyne take place with N-benzylanilines, N-alkylanilines, and N-alkylbenzylamines.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8248392 | PMC |
| http://dx.doi.org/10.1002/chem.202100238 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Construction of Bridged Benzazepines via Photo-Induced Dearomatization.
Angew Chem Int Ed Engl
January 2024
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023, China.
Bridged benzazepine scaffolds, possessing unique structural and physicochemical activities, are widespread in various natural products and drugs. The construction of these skeletons often requires elaborate synthetic effort with low efficiency. Herein, we develop a simple and divergent approach for constructing various bridged benzazepines by a photocatalytic intermolecular dearomatization of naphthalene derivatives with readily available α-amino acids.
View Article and Find Full Text PDFDivergent Radical Cyclization and Hydroaminoalkylation of -Arylacrylamides Using Photoredox Catalysis.
J Org Chem
May 2023
School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, Yunnan, China.
The ability to selectively synthesize multiple products from the same sets of substrates is a highly appealing and challenging concept in synthetic chemistry. In this manuscript, we describe the visible-light photoredox intermolecular catalysis of -arylacrylamides that are α-C-H functionalized with aryl tertiary amines. The photocatalyst acts as a chemical switch to trigger two different reaction pathways and to obtain two different products from the same starting material.
View Article and Find Full Text PDFRegio-, Diastereo-, and Enantioselective Decarboxylative Hydroaminoalkylation of Dienol Ethers Enabled by Dual Palladium/Photoredox Catalysis.
Angew Chem Int Ed Engl
May 2022
Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104, Freiburg im Breisgau, Germany.
Intermolecular photocatalytic hydroaminoalkylation (HAA) of alkenes have emerged as a powerful method for the construction of alkyl amines. Although there are some studies aiming at stereoselective photocatalytic HAA reactions, the alkenes are limited to electrophilic alkenes. Herein, we report a highly regio-, diastereo-, and enantioselective HAA of electron-rich dienol ethers and α-amino radicals derived from α-amino acids using a unified photoredox and palladium catalytic system.
View Article and Find Full Text PDFStereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines.
Chemistry
February 2022
Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26129, Oldenburg, Germany.
Intermolecular hydroaminoalkylation reactions of symmetrical and unsymmetrical alkynes with tertiary amines take place in the presence of catalytic amounts of TiBn , Ph C[B(C F ) ], and a sterically demanding aminopyridinato ligand precursor. The resulting products, synthetically and pharmaceutically useful tertiary β,γ-disubstituted allylic amines, are formed in convincing yields and with excellent stereoselectivity. Particularly promising for future applications is the fact that even the industrial side product trimethylamine can be used as a substrate.
View Article and Find Full Text PDFPhotocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines.
J Am Chem Soc
October 2021
Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.
Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA protocols are also highly sensitive to α-substitution on the amine partner, and no catalytic solutions exist for α-tertiary γ-arylamine synthesis via this approach. We report a solution to these problems using organophotoredox catalysis, enabling a direct, modular, and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!