Copper-catalyzed synthesis of 2-aminophenyl benzothiazoles: a novel approach

2018 ◽  
Vol 16 (37) ◽  
pp. 8267-8272 ◽  
Author(s):  
S. N. Murthy Boddapati ◽  
Chandra Mohan Kurmarayuni ◽  
Baby Ramana Mutchu ◽  
Ramana Tamminana ◽  
Hari Babu Bollikolla
Keyword(s):  
Nucleophilic Substitution ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Moderate Reaction ◽  
Cross Coupling Reactions ◽  
Novel Approach

Substituted 2-aminophenyl benzothiazoles have been constructed from thiourea via copper-catalyzed desulfurization/nucleophilic substitution followed by domino intra- and intermolecular C–N cross-coupling reactions under moderate reaction conditions.

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

scholarly journals Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

2018 ◽  
Vol 14 ◽  
pp. 1871-1884 ◽  
Author(s):  
Siva Sankar Murthy Bandaru ◽  
Darinka Dzubiel ◽  
Heiko Ihmels ◽  
Mohebodin Karbasiyoun ◽  
Mohamed M A Mahmoud ◽  
...  
Keyword(s):  
Emission Intensity ◽  
Binding Constants ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
Quadruplex Dna ◽  
Cross Coupling Reactions ◽  
Sonogashira Coupling Reaction

9-Arylbenzo[b]quinolizinium derivatives were prepared with base-free Suzuki–Miyaura coupling reactions between benzo[b]quinolizinium-9-trifluoroborate and selected benzenediazonium salts. In addition, the Sonogashira coupling reaction between 9-iodobenzo[b]quinolizinium and the arylalkyne derivatives yielded four novel 9-(arylethynyl)benzo[b]quinolizinium derivatives under relatively mild reaction conditions. The 9-(N,N-dimethylaminophenylethynyl)benzo[b]quinolizinium is only very weakly emitting, but the emission intensity increases by a factor >200 upon protonation, so that this derivative may operate as pH-sensitive light-up probe. Photometric and fluorimetric titrations of duplex and quadruplex DNA to 9-(arylethynyl)benzo[b]quinolizinium derivatives revealed a significant binding affinity of these compounds towards both DNA forms with binding constants ofKb= 0.2–2.2 × 105M−1.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

A novel and efficient zinc-catalyzed thioetherification of aryl halides

RSC Advances ◽  
2015 ◽  
Vol 5 (41) ◽  
pp. 32675-32678 ◽  
Author(s):  
Amrutha P. Thankachan ◽  
K. S. Sindhu ◽  
K. Keerthi Krishnan ◽  
Gopinathan Anilkumar
Keyword(s):  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions

The first Zn-catalyzed protocol for C–S cross-coupling reactions for the synthesis of substituted aryl and alkyl sulfides with good yields under mild reaction conditions is described.

PEPPSI-SONO-SP2: a new highly efficient ligand-free catalyst system for the synthesis of tri-substituted triazine derivatives via Suzuki–Miyaura and Sonogashira coupling reactions under a green approach

2016 ◽  
Vol 40 (6) ◽  
pp. 5135-5142 ◽  
Author(s):  
Motakatla Venkata Krishna Reddy ◽  
Peddiahgari Vasu Govardhana Reddy ◽  
Cirandur Suresh Reddy
Keyword(s):  
Palladium Catalyst ◽  
Cross Coupling ◽  
Catalyst System ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Green Approach ◽  
Ligand Free ◽  
Triazine Derivatives

Consecutive Suzuki–Miyaura and Sonogashira cross coupling reactions catalyzed by a new competent palladium catalyst PEPPSI-SONO-SP2 under mild and green reaction conditions.

scholarly journals Rapid Access to Diverse Potassium Acyltrifluoroborates (KATs) Through Late-Stage Chemoselective Cross-Coupling Reactions

2020 ◽  
Author(s):  
Xingwang Deng ◽  
Guan Zhou ◽  
Xiao Han ◽  
Khadim Ullah ◽  
Rajavel Srinivasan
Keyword(s):  
Late Stage ◽  
Materials Science ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Library Synthesis ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Rapid Diversification ◽  
High Yields ◽  
Opening Up

Potassium acyltrifluoroborates (KATs) are opening up new avenues in chemical biology, materials science and synthetic organic chemistry due to their intriguing reactivities. However, the synthesis of these compounds remains mostly complicated and time-consuming. This lack of a rapid and facile synthetic route has hindered the widespread adoption of KAT-based chemistry, especially in the areas of compound library synthesis and drug discovery. Herein, we have developed chemoselective Pd-catalyzed approaches for the late-stage diversification of arenes bearing pre-functionalized KATs. These approaches feature chemoselective cross-coupling, rapid diversification, functional group tolerance, mild reaction conditions, and high yields.

Sonochemistry in Transition Metal Catalyzed Cross-coupling Reactions: Recent Developments

2020 ◽  
Vol 23 (28) ◽  
pp. 3137-3153 ◽  
Author(s):  
Sankuviruthiyil M. Ujwaldev ◽  
K. R. Rohit ◽  
Sankaran Radhika ◽  
Gopinathan Anilkumar
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Reaction Rates ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Recent Developments ◽  
Ultrasound Assisted ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

: Transition metal catalyzed cross-coupling reactions have always been very important in synthetic organic chemistry due to their versatility in forming all sorts of carbon-carbon and carbon-hetero atom bonds. Incorporation of ultrasound assistance to these protocols resulted in milder reaction conditions, faster reaction rates, etc. This review focuses on the contributions made by ultrasound-assisted protocols towards transition metal catalyzed crosscoupling reactions.

Consecutive Palladium Catalyzed Reactions in One-Pot Reactions

2020 ◽  
Vol 17 (5) ◽  
pp. 559-569
Author(s):  
Ingrid Caroline Vaaland ◽  
Magne Olav Sydnes
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Homogeneous Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions

Combining palladium catalyzed reactions in one-pot reactions represents an efficient and economical use of catalyst. The Suzuki-Miyaura cross-coupling has been proven to be a reaction which can be combined with other palladium catalyzed reactions in the same pot. This mini-review will highlight some of the latest examples where Suzuki-Miyaura cross-coupling reactions have been combined with other palladium catalyzed reactions in one-pot reaction. Predominantly, examples with homogeneous reaction conditions will be discussed in addition to a few examples from the authors where Pd/C have been used as a catalyst.

Ligand-free Pd catalyzed cross-coupling reactions in an aqueous hydrotropic medium

2016 ◽  
Vol 18 (7) ◽  
pp. 1898-1911 ◽  
Author(s):  
Sanjay N. Jadhav ◽  
Arjun S. Kumbhar ◽  
Chadrashekhar V. Rode ◽  
Rajashri S. Salunkhe
Keyword(s):  
Activated Carbon ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Ligand Free

A simple, efficient and ligand-free protocol for the Suzuki–Miyaura reaction and base-free Heck–Matsuda reactions under mild reaction conditions has been developed over palladium supported on activated carbon (Pd/C) in an aqueous hydrotropic solution.

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