Three-Component Coupling Reactions of Maleimides, Thiols, and Amines: One-Step Construction of 3,4-Heteroatom-functionalized Maleimides by Copper-Catalyzed C(sp 2 )−H Thioamination

2017 ◽  
Vol 360 (1) ◽  
pp. 173-179 ◽  
Author(s):  
Zhen-Hua Yang ◽  
Hong-Ru Tan ◽  
Yu-Long An ◽  
Yu-Wei Zhao ◽  
Hao-Peng Lin ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
One Step ◽  
Three Component Coupling

scholarly journals Et3B-mediated two- and three-component coupling reactions via radical decarbonylation of α-alkoxyacyl tellurides: single-step construction of densely oxygenated carboskeletons

2015 ◽  
Vol 6 (5) ◽  
pp. 2765-2769 ◽  
Author(s):  
Masanori Nagatomo ◽  
Daigo Kamimura ◽  
Yuki Matsui ◽  
Keisuke Masuda ◽  
Masayuki Inoue
Keyword(s):  
Single Step ◽  
Coupling Reactions ◽  
One Step ◽  
Sugar Derivatives ◽  
Three Component Coupling

We devised new radical-based two- and three-component coupling reactions of sugar derivatives, and realized one-step construction of contiguously substituted polyol structures.

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

scholarly journals PEG-embedded KBr3: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

2011 ◽  
Vol 7 ◽  
pp. 1334-1341 ◽  
Author(s):  
Sanny Verma ◽  
Suman L Jain ◽  
Bir Sain
Keyword(s):  
Coupling Reaction ◽  
Recyclable Catalyst ◽  
Efficient Synthesis ◽  
Molecular Bromine ◽  
Keto Ester ◽  
One Step ◽  
High Yields ◽  
Multicomponent Coupling ◽  
Three Component Coupling

PEG-embedded potassium tribromide ([K+PEG]Br3 −) was found to be an efficient and recyclable catalyst for the synthesis of functionalized piperidines in high yields in a one step, three component coupling between aldehyde, amine and β-keto ester. At the end of the reaction the [K+PEG]Br3 − was readily regenerated from the reaction mixture by treating the residue containing [K+PEG]Br− with molecular bromine.

CuI-Catalyzed Ullmann-Type Coupling of Phenols and Thiophenols with 5-Substituted-1,2,3-triiodobenzene: Facile Synthesis of Mammary Carcinoma Inhibitor BTO-956 in One-step!

Synthesis ◽  
2021 ◽  
Author(s):  
Raed Al-Zoubi ◽  
Reem M. Altamimi ◽  
Walid K. Al-Jammal ◽  
Khaled Q. Shawakfeh ◽  
Mazhar S. Al-Zoubi ◽  
...  
Keyword(s):  
Functional Groups ◽  
Mammary Carcinoma ◽  
Coupling Reactions ◽  
Electronic Effects ◽  
Facile Synthesis ◽  
One Step ◽  
Type Coupling ◽  
Optimized Conditions

A facile and unprecedented synthesis of 2,3-diiodinated or 2,6-diiodinated diarylether/thioether derivatives through regioselective Ullmann-type cross couplings of 5-substituted-1,2,3-triiodobenzene and phenols/thiophenols is described. Remarkably, the coupling reactions are simply controlled by the type of nucleophiles and the nature of C5 substituent at 1,2,3-triiodoarenes providing the internal or terminal coupling products in high regioselectivity and good isolated yields. Noticeable steric and electronic effects were clearly observed on both 1,2,3-triiodoarene and nucleophile. The highest yields were isolated from a combination between either electron-poor 1,2,3-triiodoarenes and phenols or electron-rich 1,2,3-triiodoarenes and thiophenols. The optimized conditions were found to be suitable for several functional groups. Using this methodology, mammary carcinoma inhibitor BTO-956 is prepared in only one step with excellent regioselectivity and good isolated yield. This report discloses the first method to make 2,3-diiodinated and 2,6-diiodinated diarylethers/thioethers in one step that is efficient, regioselective, general in scope and truly remarkable precursors for other transformations.

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