A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-exo-dig annulation pathway for one-pot access to heterobiaryl frameworks

2019 ◽  
Vol 55 (100) ◽  
pp. 15069-15072 ◽  
Author(s):  
Xinwei He ◽  
Pui Ying Choy ◽  
Man Pan Leung ◽  
On Ying Yuen ◽  
Tianyi Liu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Conjugate Addition ◽  
One Pot ◽  
Coupling Strategy

Facile access to π-extended heterobiaryl compounds via a non-cross-coupling strategy has been achieved.

The synthesis of arylcyanamides: a copper-catalyzed consecutive desulfurization and C–N cross-coupling strategy

2018 ◽  
Vol 42 (2) ◽  
pp. 918-922 ◽  
Author(s):  
S. N. Murthy Boddapati ◽  
Naresh Polam ◽  
Baby Ramana Mutchu ◽  
Hari Babu Bollikolla
Keyword(s):  
Cross Coupling ◽  
One Pot ◽  
Highly Efficient ◽  
Simple Protocol ◽  
Coupling Strategy

A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thioureaviadesulphurization/C–N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described.

scholarly journals Ni-catalyzed deaminative cross-electrophile coupling of Katritzky salts with halides via C─N bond activation

2019 ◽  
Vol 5 (6) ◽  
pp. eaaw9516 ◽  
Author(s):  
Shengyang Ni ◽  
Chun-Xiao Li ◽  
Yu Mao ◽  
Jianlin Han ◽  
Yi Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Primary Amines ◽  
One Pot ◽  
Carbon Centers ◽  
Alkyl Bromides ◽  
Wide Range ◽  
Coupling Strategy ◽  
The One

The reductive cross-coupling of sp3-hybridized carbon centers represents great synthetic values and insurmountable challenges. In this work, we report a nickel-catalyzed deaminative cross-electrophile coupling reaction to construct C(sp)─C(sp3), C(sp2)─C(sp3), and C(sp3)─C(sp3) bonds. A wide range of coupling partners including aryl iodides, bromoalkynes, or alkyl bromides are stitched with alkylpyridinium salts that derived from the corresponding primary amines. The advantages of this methodology are showcased in the two-step synthesis of the key lactonic moiety of (+)-compactin and (+)-mevinolin. The one-pot procedure without isolation of alkylpyridinium tetrafluoroborate salt is also proven to be successful. This cross-coupling strategy of two electrophiles provides a highly valuable vista for the convenient installation of alkyl substituents and late functionalizations of sp3 carbons.

Tandem One Pot Asymmetric Conjugate Addition—Vinyl Triflate Formation—Cross Coupling Methodology.

ChemInform ◽  
2005 ◽  
Vol 36 (31) ◽  
Author(s):  
Rosa M. Suarez ◽  
Diego Pena ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa
Keyword(s):  
Cross Coupling ◽  
Conjugate Addition ◽  
One Pot ◽  
Vinyl Triflate

Tandem one pot asymmetric conjugate addition–vinyl triflate formation–cross coupling methodology

2005 ◽  
Vol 3 (5) ◽  
pp. 729-731 ◽  
Author(s):  
Rosa M. Suárez ◽  
Diego Peña ◽  
Adriaan J. Minnaard ◽  
Ben L. Feringa
Keyword(s):  
Cross Coupling ◽  
Conjugate Addition ◽  
One Pot ◽  
Vinyl Triflate

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>

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

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