Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions

2015 ◽  
Vol 51 (85) ◽  
pp. 15522-15525 ◽  
Author(s):  
A. L. Stein ◽  
F. N. Bilheri ◽  
G. Zeni
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Palladium Catalyzed

A powerful tool for constructing new carbon–carbon bonds via palladium-catalyzed cross-coupling reactions of unsaturated organoselenides is described.

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.

scholarly journals Recent progress in application of nanocatalysts for carbonylative Suzuki cross-coupling reactions

RSC Advances ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 2112-2125
Author(s):  
Inci Söğütlü ◽  
Evan Abdulkarim Mahmood ◽  
Saeid Ahmadizadeh Shendy ◽  
Saeideh Ebrahimiasl ◽  
Esmail Vessally
Keyword(s):  
Carbon Monoxide ◽  
Recent Progress ◽  
Cross Coupling ◽  
Suzuki Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

Cross-coupling of aryl halides and arylboronic acids in the presence of carbon monoxide, also called carbonylative Suzuki coupling, to form two new carbon–carbon bonds in the production of synthetically and biologically important biaryl ketones, has been widely studied.

(E)-α-Iodovinylstannanes as Convenient Precursors for Stereoselective Synthesis of Trisubstituted Alkenes

2003 ◽  
Vol 2003 (8) ◽  
pp. 465-467 ◽  
Author(s):  
Mingzhong Cai ◽  
Hongde Ye ◽  
Hong Zhao ◽  
Caisheng Song
Keyword(s):  
Stereoselective Synthesis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Olefinic Carbon ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Trisubstituted Alkenes

Based on the different reactivities of iodo-groups and tributylstannyl groups, ( E)-α-iodovinylstannanes can undergo sequential cross-coupling reactions in the presence of a palladium(0) catalyst to form two carbon-carbon bonds to the same olefinic carbon leading to trisubstituted alkenes stereoselectively.

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.

C -Glycosylated Phenylalanine Synthesis by Palladium-Catalyzed Cross-Coupling Reactions

Synlett ◽  
2003 ◽  
pp. 1834-1837 ◽  
Author(s):  
Nadège Lubin-Germain ◽  
Jacques Augé ◽  
Valérie Boucard ◽  
Karen Larrieu ◽  
Jacques Uziel
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed
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