DFT studies on the mechanism of palladium-catalyzed carbon–silicon cleavage for the synthesis of benzosilole derivatives

2014 ◽  
Vol 43 (29) ◽  
pp. 11138-11144 ◽  
Author(s):  
Wen-Jie Chen ◽  
Zhenyang Lin
Keyword(s):  
Dft Calculations ◽  
Coupling Reactions ◽  
Dft Studies ◽  
Detailed Mechanism ◽  
Palladium Catalyzed ◽  
Intermolecular Coupling

DFT calculations have been carried out to study the detailed mechanism of Pd-catalyzed intermolecular coupling reactions of 2-silylaryl bromides with alkynes via selective cleavage of C(sp3)–Si bonds.

Palladium-catalyzed synthesis of pyrimidine substituted diaryl ethers through Suzuki Miyaura coupling reactions: Experimental and DFT studies

Optik ◽  
2020 ◽  
Vol 219 ◽  
pp. 165285
Author(s):  
Ilham Khan ◽  
Muhammad Khalid ◽  
Muhammad Adeel ◽  
Muhammad Usman Khan ◽  
Muhammad Sohail Khan ◽  
...  
Keyword(s):  
Coupling Reactions ◽  
Dft Studies ◽  
Diaryl Ethers ◽  
Palladium Catalyzed

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.

Formal Total Syntheses of Crocacin A-D

2005 ◽  
Vol 70 (10) ◽  
pp. 1696-1708 ◽  
Author(s):  
Magnus Besev ◽  
Christof Brehm ◽  
Alois Fürstner
Keyword(s):  
Natural Products ◽  
Aldol Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Total Syntheses ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
The Common ◽  
Selective Addition

A concise route to the common polyketide fragment5of crocacin A-D (1-4) is presented which has previously been converted into all members of this fungicidal and cytotoxic family of dipeptidic natural products by various means. Our synthesis features asyn-selective titanium aldol reaction controlled by a valinol-derived auxiliary, a zinc-mediated, palladium-catalyzedanti-selective addition of propargyl mesylate10to the chiral aldehyde9, as well as a comparison of palladium-catalyzed Stille and Suzuki cross-coupling reactions for the formation of the diene moiety of the target.

Highly Efficient Four-Component Synthesis of 4(3H)-Quinazolinones: Palladium-Catalyzed Carbonylative Coupling Reactions

2013 ◽  
Vol 53 (5) ◽  
pp. 1420-1424 ◽  
Author(s):  
Lin He ◽  
Haoquan Li ◽  
Helfried Neumann ◽  
Matthias Beller ◽  
Xiao-Feng Wu
Keyword(s):  
Coupling Reactions ◽  
Highly Efficient ◽  
Palladium Catalyzed

scholarly journals A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy Towards Oxazocine Scaffolds

Synlett ◽  
2021 ◽  
Author(s):  
Julian Garrec ◽  
Alexis Archambeau ◽  
Anaïs Scuiller ◽  
Xueyang Liu ◽  
Marie Cordier
Keyword(s):  
Dft Calculations ◽  
Palladium Catalyzed

AbstractA Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

Base-Free Synthesis and Synthetic Application of Novel 3-(organochalcogenyl)prop-2-yn-1-yl Esters: Promising Anticancer Agents

Synthesis ◽  
2021 ◽  
Author(s):  
Fabiane Gritzenco ◽  
Jean Carlo Kazmierczak ◽  
Thiago Anjos ◽  
Adriane Sperança ◽  
Maura Luise Bruckchem Peixoto ◽  
...  
Keyword(s):  
Anticancer Agents ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Chalcogen Bond ◽  
Cross Coupling Reactions ◽  
Air Atmosphere ◽  
Carbon Carbon Bonds ◽  
Palladium Catalyzed ◽  
Synthetic Application

This manuscript portrays the CuI-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynyl esters and diorganyl dichalcogenides by using DMSO as solvent, at room temperature, under base-free and open-to-air atmosphere. Generally, the reactions have proceeded very smoothly, being tolerant to range of substituents present in both substrates, affording the novel 3-(organochalcogenyl)prop-2-yn-1-yl esters in moderate to good yields. Noteworthy, the 3-(butylselanyl)prop-2-yn-1-yl benzoate proved to be useful as synthetic precursor in palladium-catalyzed Suzuki and Sonogashira type cross-coupling reactions by replacing the carbon-chalcogen bond by new carbon-carbon bonds. Moreover, the 3-(phenylselanyl)prop-2-yn-1-yl benzoate has shown promising in vitro activity against glioblastoma cancer cells.

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