Synthesis of chiral branched allylamines through dual photoredox/nickel catalysis

2021 ◽  
Vol 19 (39) ◽  
pp. 8578-8585
Author(s):  
Mateusz Garbacz ◽  
Sebastian Stecko
Keyword(s):  
Cross Coupling ◽  
Nickel Catalysis ◽  
New Approach ◽  
Alkyl Bromides

This work describes a new approach for the preparation of allylamines via cross-coupling of alkyl bromides with simple 3-bromoallylamines by merging the photoredox approach and Ni catalysis.

Cross‐Coupling Reaction of Alkenyl Sulfoximines and Alkenyl Aminosulfoxonium Salts with Organozincs by Dual Nickel Catalysis and Lewis Acid Promotion

2019 ◽  
Vol 25 (35) ◽  
pp. 8371-8386 ◽  
Author(s):  
Irene Erdelmeier ◽  
Gerd Bülow ◽  
Chang‐Wan Woo ◽  
Jürgen Decker ◽  
Gerhard Raabe ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Nickel Catalysis ◽  
Cross Coupling Reaction

Reductive Alkylation of Alkenyl Acetates with Alkyl Bromides by Nickel Catalysis

2021 ◽  
Author(s):  
Rong-De He ◽  
Yunfei Bai ◽  
Guan-Yu Han ◽  
Zhen-Zhen Zhao ◽  
Xiaobo Pang ◽  
...  
Keyword(s):  
Nickel Catalysis ◽  
Reductive Alkylation ◽  
Alkyl Bromides

scholarly journals Synthesis of Functionalized Cannabilactones

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 684
Author(s):  
Yingpeng Liu ◽  
Thanh C. Ho ◽  
Mohammed Baradwan ◽  
Maria Pascual Lopez-Alberca ◽  
Christos Iliopoulos-Tsoutsouvas ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
New Approach ◽  
Structural Modifications ◽  
Cross Coupling Reaction ◽  
One Step

A new approach to synthesize cannabilactones using Suzuki cross-coupling reaction followed by one-step demethylation-cyclization is presented. The two key cannabilactone prototypes AM1710 and AM1714 were obtained selectively in high overall yields and in a lesser number of synthetic steps when compared to our earlier synthesis. The new approach expedited the synthesis of cannabilactone analogs with structural modifications at the four potential pharmacophoric regions.

Nickel-catalyzed alkyl–alkyl cross-coupling reactions of non-activated secondary alkyl bromides with aldehydes as alkyl carbanion equivalents

2019 ◽  
Vol 55 (19) ◽  
pp. 2793-2796 ◽  
Author(s):  
Chenghao Zhu ◽  
Junliang Zhang
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Alkyl Bromides

A novel nickel-catalyzed alkyl–alkyl cross coupling of non-activated secondary alkyl bromides with aldehydes via hydrazone intermediates has been developed.

scholarly journals A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

2019 ◽  
Vol 15 ◽  
pp. 2569-2576 ◽  
Author(s):  
Thines Kanagasundaram ◽  
Antje Timmermann ◽  
Carsten S Kramer ◽  
Klaus Kopka
Keyword(s):  
Free Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Stimulated Emission ◽  
New Approach ◽  
Cross Coupling Reaction ◽  
Optimal Coupling ◽  
Sensor Molecules ◽  
Optimized Conditions ◽  
Coupling Partner

Background: Silicon rhodamines are of particular interest because of their advantageous dye properties (fluorescence- and biostability, quantum efficiency, tolerance to photobleaching). Therefore, silicon rhodamines find frequent application in STED (stimulated emission depletion) microscopy, as sensor molecules for, e.g., ions and as fluorophores for the optical imaging of tumors. Different strategies were already employed for their synthesis. Because of just three known literature examples in which Suzuki–Miyaura cross couplings gave access to silicon rhodamines in poor to moderate yields, we wanted to improve these first valuable experimental results. Results: The preparation of the xanthene triflate was enhanced and several boron sources were screened to find the optimal coupling partner. After optimization of the palladium catalyst, different substituted boroxines were assessed to explore the scope of the Pd-catalyzed cross-coupling reaction. Conclusions: A number of silicon rhodamines were synthesized under the optimized conditions in up to 91% yield without the necessity of HPLC purification. Moreover, silicon rhodamines functionalized with free acid moieties are directly accessible in contrast to previously described methods.

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