Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions To Give Chalcones

2010 ◽  
Vol 49 (31) ◽  
pp. 5284-5288 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Coupling Reactions ◽  
Heck Reactions ◽  
Palladium Catalyzed

ChemInform Abstract: Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions to Give Chalcones.

ChemInform ◽  
2010 ◽  
Vol 41 (49) ◽  
pp. no-no
Author(s):  
Xiao-Feng Wu ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Coupling Reactions ◽  
Heck Reactions ◽  
Palladium Catalyzed

scholarly journals Palladium-Catalyzed Mizoroki–Heck and Copper-Free Sonogashira Coupling Reactions in Water Using Thermoresponsive Polymer Micelles

Polymers ◽  
2021 ◽  
Vol 13 (16) ◽  
pp. 2717
Author(s):  
Noriyuki Suzuki ◽  
Shun Koyama ◽  
Rina Koike ◽  
Nozomu Ebara ◽  
Rikito Arai ◽  
...  
Keyword(s):  
Good Yield ◽  
Diblock Copolymers ◽  
Extraction Process ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Polymer Micelles ◽  
Heck Reactions ◽  
Thermoresponsive Polymer ◽  
Palladium Catalyzed ◽  
Efficient Extraction

A few kinds of thermoresponsive diblock copolymers have been synthesized and utilized for palladium-catalyzed coupling reactions in water. Poly(N-isopropylacrylamide) (PNIPAAm) and poly(N,N-diethylacrylamide) (PDEAAm) are employed for thermoresponsive segments and poly(sodium 4-styrenesulfonate) (PSSNa) and poly(sodium 2-acrylamido-methylpropanesulfonate) (PAMPSNa) are employed for hydrophilic segments. Palladium-catalyzed Mizoroki–Heck reactions are performed in water and the efficiency of the extraction process is studied. More efficient extraction was observed for the PDEAAm copolymers when compared with the PNIPAAm copolymers and conventional surfactants. In the study of the Sonogashira coupling reactions in water, aggregative precipitation of the products was observed. Washing the precipitate with water gave the product with satisfactory purity with a good yield.

scholarly journals Dimethylisosorbide (DMI) as a Bio-Derived Solvent for Pd-Catalyzed Cross-Coupling Reactions

Synlett ◽  
2018 ◽  
Vol 29 (17) ◽  
pp. 2293-2297 ◽  
Author(s):  
Allan Watson ◽  
Kirsty Wilson ◽  
Jane Murray ◽  
Helen Sneddon ◽  
Craig Jamieson
Keyword(s):  
Chemical Industry ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Heck Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Palladium-catalyzed bond-forming reactions, such as the ­Suzuki–Miyaura and Mizoroki–Heck reactions, are some of the most broadly utilized reactions within the chemical industry. These reactions frequently employ hazardous solvents; however, to adhere to increasing sustainability pressures and restrictions regarding the use of such solvents, alternatives are highly sought after. Here we demonstrate the utility of dimethyl isosorbide (DMI) as a bio-derived solvent in several benchmark Pd-catalyzed reactions: Suzuki–Miyaura (13 examples, 62–100% yield), Mizoroki–Heck (13 examples, 47–91% yield), and Sonogashira (12 examples, 65–98% yield).

Aryl-Decarboxylation Reactions Catalyzed by Palladium: Scope and Mechanism

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 365-377 ◽  
Author(s):  
Ryan A. Daley ◽  
Joseph J. Topczewski
Keyword(s):  
Carboxylic Acids ◽  
Boronic Acid ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Heck Reactions ◽  
Cross Coupling Reactions ◽  
Related Family ◽  
Organometallic Precursor ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Palladium-catalyzed cross-couplings and related reactions have enabled many transformations essential to the synthesis of pharmaceuticals, agrochemicals, and organic materials. A related family of reactions that have received less attention are decarboxylative functionalization reactions. These reactions replace the preformed organometallic precursor (e.g., boronic acid or organostannane) with inexpensive and readily available carboxylic acids for many palladium-catalyzed reactions. This review focuses on catalyzed reactions where the elementary decarboxylation step is thought to occur at a palladium center. This review does not include decarboxylative reactions where decarboxylation is thought to be facilitated by a second metal (copper or silver) and is specifically limited to (hetero)arenecarboxylic acids. This review includes a discussion of oxidative Heck reactions, protodecarboxylation reactions, and cross-coupling reactions among others.1 Introduction2 Oxidative Heck Reactions3 Protodecarboxylation Reactions4 Cross-Coupling Reactions5 Other Reactions6 Conclusion

Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions To Give Chalcones

2010 ◽  
Vol 122 (31) ◽  
pp. 5412-5416 ◽  
Author(s):  
Xiao-Feng Wu ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Coupling Reactions ◽  
Heck Reactions ◽  
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
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