scholarly journals Mild Copper-Catalyzed, l-Proline-Promoted Cross-Coupling of Methyl 3-Amino-1-benzothiophene-2-carboxylate

Molecules ◽  
2021 ◽  
Vol 26 (22) ◽  
pp. 6822
Author(s):  
Vilija Kederienė ◽  
Indrė Jaglinskaitė ◽  
Paulina Voznikaitė ◽  
Jolanta Rousseau ◽  
Patrick Rollin ◽  
...  
Keyword(s):  
Nmr Spectroscopy ◽  
Chemical Modification ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Moderate Temperature ◽  
Aromatic Heterocycles ◽  
Aryl Iodides ◽  
High Yields

Cu-catalyzed N-arylation is a useful tool for the chemical modification of aromatic heterocycles. Herein, an efficient carbon–nitrogen cross-coupling of methyl 3-amino-1-benzothiophene-2-carboxylate with a range of (hetero)aryl iodides using CuI, l-proline and Cs2CO3 in dioxane at moderate temperature is described. The procedure is an extremely general, relatively cheap, and experimentally simple way to afford the N-substituted products in moderate to high yields. The structures of the new heterocyclic compounds were confirmed by NMR spectroscopy and HRMS investigation.

Ferromagnetic Chain Based on Verdazyl-Nitroxide Diradical

2020 ◽  
Author(s):  
Evgeny Tretyakov ◽  
Svetlana Zhivetyeva ◽  
Pavel Petunin ◽  
Dmitry Gorbunov ◽  
Nina Gritsan ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Ferromagnetic Coupling ◽  
Nitronyl Nitroxide ◽  
Triplet Ground State ◽  
One Dimensional ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Ferromagnetic Chain ◽  
High Yields

<p>Verdazyl-nitroxide diradicals were synthesized using the palladium-catalyzed cross-coupling reaction of the corresponding iodoverdazyls with a nitronyl nitroxide-2-ide gold(I) complex with high yields (up to 82%). The synthesized diradicals were found to be highly thermally stable and have a singlet (D<i>E</i><sub>ST</sub> » -64 cm<sup>–1</sup>) or triplet ground state (D<i>E</i><sub>ST</sub> ³ 25 and 100 cm<sup>–1</sup>), depending on which canonical hydrocarbon diradical type they belong to. Upon crystallization, triplet diradicals form unique one-dimensional (1D) spin <i>S</i> = 1 chains of organic diradicals with intrachain ferromagnetic coupling of <i>J</i>′/<i>k</i><sub>B</sub> from 3 to 6 K.</p>

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

Modular, Stereocontrolled Cβ–H/Cα–C Activation of Alkyl Carboxylic Acids

2019 ◽  
Author(s):  
Ming Shang ◽  
Karla S. Feu ◽  
Julien C. Vantourout ◽  
Lisa M. Barton ◽  
Heather L. Osswald ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Heterocyclic Compounds ◽  
Cross Coupling ◽  
Building Blocks ◽  
Enantioselective Synthesis ◽  
Carbon Centers ◽  
Drug Candidates ◽  
Rapid Diversification ◽  
Directing Group ◽  
Compound Series

<div> <div> <div> <p>The union of two powerful transformations, directed C–H activation and decarboxylative cross-coupling, for the enantioselective synthesis of vicinally functionalized alkyl, carbocyclic, and heterocyclic compounds is described. Starting from simple carboxylic acid building blocks, this modular sequence exploits the residual directing group to access more than 50 scaffolds that would be otherwise extremely difficult to prepare. The tactical use of these two transformations accomplishes a formal vicinal difunctionalization of carbon centers in a way that is modular and thus amenable to rapid diversity incorporation. A simplification of routes to known preclinical drug candidates is presented along with the rapid diversification of an antimalarial compound series. </p> </div> </div> </div>

scholarly journals Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

2021 ◽  
Author(s):  
Travis DeLano ◽  
Sara Dibrell ◽  
Caitlin R. Lacker ◽  
Adam Pancoast ◽  
Kelsey Poremba ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Mild Conditions ◽  
Aryl Iodides ◽  
Reaction Proceeds

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities....

Photoinduced Cross-Coupling of Aryl Iodides with Alkenes

2021 ◽  
Author(s):  
Yuliang Liu ◽  
Haoyu Li ◽  
Shunsuke Chiba
Keyword(s):  
Cross Coupling ◽  
Aryl Iodides

scholarly journals Iron/copper-catalyzed C–C cross-coupling of aryl iodides with terminal alkynes

2008 ◽  
Vol 49 (41) ◽  
pp. 5961-5964 ◽  
Author(s):  
Chandra M. Rao Volla ◽  
Pierre Vogel
Keyword(s):  
Cross Coupling ◽  
Terminal Alkynes ◽  
Iron Copper ◽  
Aryl Iodides

An Efficient Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides

2011 ◽  
Vol 2011 (9) ◽  
pp. 1776-1781 ◽  
Author(s):  
Hsin-Lun Kao ◽  
Chin-Keng Chen ◽  
Yu-Jen Wang ◽  
Chin-Fa Lee
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Iodides ◽  
Cross Coupling Reaction

Palladium Catalyzed Synthesis of Phenylquinoxaline-Alkyne Derivatives via Sonogashira Cross Coupling Reaction

2021 ◽  
Vol 43 (1) ◽  
pp. 95-95
Author(s):  
Rifhat Bibi Rifhat Bibi ◽  
Muhammad Yaseen Muhammad Yaseen ◽  
Haseen Ahmad Haseen Ahmad ◽  
Ismat Ullah Khan Ismat Ullah Khan ◽  
Shaista Parveen Shaista Parveen ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Reaction ◽  
Terminal Alkynes ◽  
Vinyl Halides ◽  
Sonogashira Coupling Reaction ◽  
Quinoxaline Derivatives ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Alkyne Derivatives

Transition metals mediated cross coupling methodologies provide an extremely powerful versatile pathway in organic syntheses undoubtedly, a facile route for syntheses and derivatization of biologically important heterocycles from easily available precursors. Sonogashira coupling reaction, a leading method to Csp-Csp2 bond formation is one of the most important and rapid pathways to couple aryl/vinyl halides with terminal alkynes. Current research study deals with the synthesis of alkyne substituted quinoxaline derivatives. The quinoxalines class of aromatic heterocycles exhibits a wide variety of important biological potencies. Palladium catalyzed cross coupling process provided an effective synthetic practice for the synthesis of alkyne derivatives of quinoxaline. Vareity of terminal alkynes were coupled with 2-(4-bromophenyl)quinoxaline under optimized conditions for Sonogashira reaction, affording alkyne substituted quinoxaline derivatives in high yields. The optimized reaction conditions for coupling of range of terminal alkyne with quinoxaline basic core render this process significant for designing of medicinally interesting precursors.

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