Palladium-Catalyzed Asymmetric Heck–Matsuda Reaction of 1,4-Dihydroquinolines with Aryl Diazonium Salts

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3269-3276
Author(s):  
Ze-Zhen Jiang ◽  
Yang-Jie Jiang ◽  
Juan Du ◽  
Di Chen ◽  
Chang-Hua Ding ◽  
...  
Keyword(s):  
Optically Active ◽  
Diazonium Salts ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
High Yields

A palladium-catalyzed asymmetric Heck–Matsuda reaction of N-Boc-1,4-dihydroquinolines and aryl diazonium tetrafluoroborates is realized in moderate to high yields and with high enantioselectivities. The method provides an efficient route to access optically active 2-arylhydroquinolines.

The Synthesis of Novel Oligomer 4,8-Di(4-hexyl-2-thienyl)-2λ4δ2-Benzo[1,2-c;4,5-c’]bis[1,2,5]-Thiadiazole

2012 ◽  
Vol 602-604 ◽  
pp. 696-699
Author(s):  
Xiao Xiao Zhuang ◽  
Xiao Long Lei ◽  
Xiao Xia Sun
Keyword(s):  
Side Chains ◽  
Coupling Reactions ◽  
Low Bandgap ◽  
Palladium Catalyzed ◽  
Efficient Route ◽  
High Yields ◽  
Bandgap Materials

Heterocyclic oligomer based on BBT bearing solubilizing side chains have been synthesized in high yields over six steps from readily available starting materials. This approach offers a much milder, shorter, and more efficient route to BBT derivatives than current methods. This unit can then be used in the synthesis of low bandgap materials via palladium-catalyzed coupling reactions.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

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>

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.

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

Synthesis ◽  
2021 ◽  
Author(s):  
Antonella Goggiamani ◽  
Antonia Iazzetti ◽  
Antonio Arcadi ◽  
Andrea Calcaterra ◽  
Marco Chiarini ◽  
...  
Keyword(s):  
Boronic Acids ◽  
Experimental Procedure ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Reaction Works

AbstractThe palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Palladium-Catalyzed Oxidation-Hydroxylation and Oxidation-Methoxylation­ of N-Boc Indoles for the Synthesis of 3-Oxoindolines

Synthesis ◽  
2017 ◽  
Vol 49 (16) ◽  
pp. 3662-3669 ◽  
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen ◽  
Liang-Guang Wang ◽  
Dan Yang ◽  
Zhi Li
Keyword(s):  
Tert Butyl ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Catalyzed Oxidation

The palladium-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles for the synthesis of tert-butyl 2-hydroxy(methoxy)-3-oxoindoline-1-carboxylates and their derivatives is developed. The process occurs readily using PdCl2 as the catalyst and acetonitrile as the solvent to afford 3-oxoindolines in moderate to high yields. A mechanism for this Pd-catalyzed oxidation-hydroxylation and oxidation-methoxylation of N-Boc indoles is proposed.

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