Sequential One‐Pot Coupling Reactions of Diiodobenzenes, Propiolic Acid, and Aryl Halides for the Synthesis of Diarylalkynyl Arenes

2020 ◽  
Vol 9 (11) ◽  
pp. 1754-1759
Author(s):  
Beomseok Ryu ◽  
Jonghoon Oh ◽  
Sunwoo Lee
2011 ◽  
Vol 66 (8) ◽  
pp. 833-836
Author(s):  
Zhiping Che ◽  
Hui Xu

An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.


2018 ◽  
Vol 2018 (1) ◽  
pp. 120-125 ◽  
Author(s):  
Pavel S. Gribanov ◽  
Yulia D. Golenko ◽  
Maxim A. Topchiy ◽  
Lidiya I. Minaeva ◽  
Andrey F. Asachenko ◽  
...  

2020 ◽  
Author(s):  
David Charboneau ◽  
Emily L. Barth ◽  
Nilay Hazari ◽  
Mycah R. Uehling ◽  
Susan L. Zultanski

A new dual catalytic system for cross-electrophile coupling reactions between aryl and alkyl halides that features a Ni catalyst, a Co co-catalyst, and a mild homogeneous reductant, is described. This is a unique combination of reagents for cross-electrophile coupling reactions, which results in one of the most versatile systems reported to date. For example, the coupling of aryl bromides and aryl iodides with alkyl bromides, alkyl iodides, alkyl mesylates, and benzyl chlorides is demonstrated under similar reaction conditions. The system is tolerant of numerous functional groups and is capable of coupling heteroaryl halides, di-ortho-substituted aryl halides, pharmaceutically relevant drug-like aryl halides, and a diverse range of alkyl halides. Additionally, the dual catalytic platform facilitates a series of novel one-pot three-component cross-electrophile coupling reactions of bromo(iodo)arenes with two distinct alkyl halides. Mechanistic studies indicate that the Ni catalyst activates the aryl halide electrophile, while the Co catalyst activates the alkyl electrophile.


2020 ◽  
Author(s):  
David Charboneau ◽  
Emily L. Barth ◽  
Nilay Hazari ◽  
Mycah R. Uehling ◽  
Susan L. Zultanski

A new dual catalytic system for cross-electrophile coupling reactions between aryl and alkyl halides that features a Ni catalyst, a Co co-catalyst, and a mild homogeneous reductant, is described. This is a unique combination of reagents for cross-electrophile coupling reactions, which results in one of the most versatile systems reported to date. For example, the coupling of aryl bromides and aryl iodides with alkyl bromides, alkyl iodides, alkyl mesylates, and benzyl chlorides is demonstrated under similar reaction conditions. The system is tolerant of numerous functional groups and is capable of coupling heteroaryl halides, di-ortho-substituted aryl halides, pharmaceutically relevant drug-like aryl halides, and a diverse range of alkyl halides. Additionally, the dual catalytic platform facilitates a series of novel one-pot three-component cross-electrophile coupling reactions of bromo(iodo)arenes with two distinct alkyl halides. Mechanistic studies indicate that the Ni catalyst activates the aryl halide electrophile, while the Co catalyst activates the alkyl electrophile.


2019 ◽  
Author(s):  
Victor Bloemendal ◽  
Floris P. J. T. Rutjes ◽  
Thomas J. Boltje ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
...  

<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>


2019 ◽  
Author(s):  
Randolph Escobar ◽  
Jeffrey Johannes

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>


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