Sequential Sonogashira/intramolecular aminopalladation/cross-coupling of ortho-ethynyl-anilines catalyzed by a single Palladium source: rapid access to 2,3-diarylindoles

2021 ◽  
Author(s):  
Jun Zhang ◽  
Ye Liu ◽  
Gendi Wang ◽  
Jiwei Wang ◽  
Xiang Cheng
Keyword(s):  
Cross Coupling ◽  
One Pot ◽  
Rapid Access ◽  
Aryl Iodides

We have developed a practical and efficient one-pot protocol for the synthesis of 2,3-diarylindoles via Pd-catalyzed bis-arylative cyclization of various o-ethynylanilines with aryl iodides. Mechanism studies showed that a Pd-catalyzed...

Short syntheses of 1-substituted dibenzothiophene derivatives

2021 ◽  
Vol 19 (9) ◽  
pp. 2000-2007
Author(s):  
Erin N. Welsh ◽  
Katherine N. Robertson ◽  
Alexander W. H. Speed
Keyword(s):  
Cross Coupling ◽  
One Pot ◽  
Chiral Amine ◽  
Rapid Access

A one-pot double benzyne cascade allows rapid access to 1-substituted dibenzothiophene derivatives, including cross-coupling partners and a chiral amine.

Ligand-Controlled Chemoselective One-Pot Synthesis of Dibenzothiazepinones and Dibenzoxazepinones via Twice Copper-Catalyzed Cross-Coupling

Synlett ◽  
2017 ◽  
Vol 28 (10) ◽  
pp. 1201-1208 ◽  
Author(s):  
Lanting Xu ◽  
Xianhua Pan ◽  
Yanyu Chen ◽  
Qiujun Peng ◽  
Rong Zhang ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Psychotropic Drug ◽  
Cross Coupling ◽  
One Pot ◽  
Highly Efficient ◽  
Rapid Access ◽  
One Pot Synthesis

A highly efficient and generally applicable protocol, starting from 2-bromobenzamides and 2-bromo(thio)phenols via twice copper-catalyzed couplings to afford dibenzothiazepines and dibenzoxazepinones has been developed. High levels of yield and chemoselectivity are achieved in a single-pot reaction by using an appropriate ligand. Moreover, this facile methodology allows rapid access to a variety of bio­active compounds and known psychotropic drug, which should broaden its application in organic synthesis.

One-Pot Palladium-Catalyzed Cross-Coupling Reaction of Aryl Iodides with Stannylarsanes and Stannylstibanes

2003 ◽  
Vol 5 (15) ◽  
pp. 2731-2734 ◽  
Author(s):  
Mariana Bonaterra ◽  
Sandra E. Martín ◽  
Roberto A. Rossi
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed

A triazine-based covalent organic framework/palladium hybrid for one-pot silicon-based cross-coupling of silanes and aryl iodides

RSC Advances ◽  
2015 ◽  
Vol 5 (51) ◽  
pp. 41017-41024 ◽  
Author(s):  
Sha Lin ◽  
Yuxia Hou ◽  
Xiao Deng ◽  
Haoliang Wang ◽  
Shuzhuang Sun ◽  
...  
Keyword(s):  
Hybrid Material ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Covalent Organic Framework ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
Silicon Based ◽  
Excellent Selectivity ◽  
Organic Framework

A palladium/COF hybrid material could efficiently catalyze the silicon-based one-pot cross-coupling reaction of silanes and aryl iodides with excellent selectivity.

Nanoporous palladium catalyzed silicon-based one-pot cross-coupling reaction of aryl iodides with organosilanes

2014 ◽  
Vol 4 (6) ◽  
pp. 1734-1737 ◽  
Author(s):  
Zhiwen Li ◽  
Sha Lin ◽  
Lisha Ji ◽  
Zhonghua Zhang ◽  
Xiaomei Zhang ◽  
...  
Keyword(s):  
Heterogeneous Catalyst ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
One Pot ◽  
Aryl Iodides ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
Silicon Based

One-pot cross-coupling of aryl iodides with organosilanes is realized using dealloyed nanoporous palladium as a sustainable and heterogeneous catalyst.

A Revised Modular Approach to D8-THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  
Keyword(s):  
Biological Activity ◽  
Late Stage ◽  
Medicinal Chemistry ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
One Pot ◽  
Biologically Relevant ◽  
Cross Coupling Reactions ◽  
Chemistry Research

<p>In this manuscript we describe a modular pathway to synthesize biologically relevant (–)-<i>trans</i>-Δ<sup>8</sup>-THC derivatives, which can be used to modulate the pharmacologically important CB<sub>1</sub> and CB<sub>2</sub> receptors. This pathway involves a one-pot Friedel-Crafts alkylation/cyclization protocol, followed by Suzuki-Miyaura cross-coupling reactions and gives rise to a series of new Δ<sup>8</sup>-THC derivatives. In addition, we demonstrate using extensive NMR evidence that similar halide-substituted Friedel-Crafts alkylation/cyclization products in previous articles were wrongly assigned as the para-isomers, which also has consequence for the assignment of the subsequent cross-coupled products and interpretation of their biological activity. </p> <p>Considering the importance of the availability of THC derivatives in medicinal chemistry research and the fact that previously synthesized compounds were wrongly assigned, we feel this research is describing a straightforward pathway into new cannabinoids.</p>

Metal-Free Photoredox-Catalyzed C–H/C–H Coupling of Arenes Enabled by Interrupted Pummerer Activation

2019 ◽  
Author(s):  
Miles Aukland ◽  
Mindaugas Šiaučiulis ◽  
Adam West ◽  
Gregory Perry ◽  
David Procter
Keyword(s):  
Natural Product ◽  
Selective Reduction ◽  
Cross Coupling ◽  
One Pot ◽  
Complex Molecules ◽  
Pummerer Reaction ◽  
Metal Free ◽  
Bond Forming ◽  
Coupling Partner ◽  
Bioactive Natural Product

<p>Aryl–aryl cross-coupling constitutes one of the most widely used procedures for the synthesis of high-value materials, ranging from pharmaceuticals to organic electronics and conducting polymers. The assembly of (hetero)biaryl scaffolds generally requires multiple steps; coupling partners must be functionalized before the key bond-forming event is considered. Thus, the development of selective C–H arylation processes in arenes, that side-step the need for prefunctionalized partners, is crucial for streamlining the construction of these key architectures. Here we report an expedient, one-pot assembly of (hetero)biaryl motifs using photocatalysis and two non-prefunctionalized arene partners. The approach is underpinned by the activation of a C–H bond in an arene coupling partner using the interrupted Pummerer reaction. A unique pairing of the organic photoredox catalyst and the intermediate dibenzothiophenium salts enables highly selective reduction in the presence of sensitive functionalities. The utility of the metal-free, one-pot strategy is exemplified by the synthesis of a bioactive natural product and the modification of complex molecules of societal importance.</p>

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