Boronate Ester Bullvalenes

2019 ◽  
Author(s):  
Harshal Patel ◽  
Thanh Huyen Tran ◽  
Christopher Sumby ◽  
Lukáš Pašteka ◽  
Thomas Fallon
Keyword(s):  
Crystal Lattice ◽  
Late Stage ◽  
Cross Coupling ◽  
Shape Selectivity ◽  
Solution Phase ◽  
Coupling Reactions ◽  
General Shape ◽  
X Ray ◽  
Boronate Ester ◽  
Cross Coupling Reactions

<div> <div> <div> <p>Boronate ester bullvalenes are now accessible in two to four operationally simple steps. This unlocks late-stage diversification through Suzuki cross-coupling reactions to give mono-, di-, and tri-substituted bullvalenes. Moreover, a linchpin strategy enables pre-programmed installation of two different substituents. Analysis of solution phase isomer distributions and single crystal X-ray structures reveals that isomer preference in the crystal lattice is due to general shape selectivity. </p> </div> </div> </div>

Boronate Ester Bullvalenes

2019 ◽  
Author(s):  
Harshal Patel ◽  
Thanh Huyen Tran ◽  
Christopher Sumby ◽  
Lukáš Pašteka ◽  
Thomas Fallon
Keyword(s):  
Crystal Lattice ◽  
Late Stage ◽  
Cross Coupling ◽  
Shape Selectivity ◽  
Solution Phase ◽  
Coupling Reactions ◽  
General Shape ◽  
X Ray ◽  
Boronate Ester ◽  
Cross Coupling Reactions

<div> <div> <div> <p>Boronate ester bullvalenes are now accessible in two to four operationally simple steps. This unlocks late-stage diversification through Suzuki cross-coupling reactions to give mono-, di-, and tri-substituted bullvalenes. Moreover, a linchpin strategy enables pre-programmed installation of two different substituents. Analysis of solution phase isomer distributions and single crystal X-ray structures reveals that isomer preference in the crystal lattice is due to general shape selectivity. </p> </div> </div> </div>

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>

scholarly journals Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

2010 ◽  
Vol 6 ◽  
Author(s):  
Tilman Lechel ◽  
Irene Brüdgam ◽  
Hans-Ulrich Reissig
Keyword(s):  
Crystal Structure ◽  
Crystal Packing ◽  
Cross Coupling ◽  
Crystal Structure Analysis ◽  
Coupling Reactions ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Fluorescence Measurements ◽  
Subsequent Conversion ◽  
Palladium Catalyzed

A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequent conversion into bis(perfluoroalkanesulfonate)s were smoothly achieved. The obtained compounds were used as substrates for palladium-catalyzed coupling reactions. Fluorescence measurements of the biscoupled products showed a maximum of emission in the violet region of the spectrum.

scholarly journals A Revised Modular Approach to (-)-trans -Δ8 -THC and Derivatives Through Late-Stage Suzuki-Miyaura Cross-Coupling Reactions

2019 ◽  
Vol 2019 (12) ◽  
pp. 2289-2296 ◽  
Author(s):  
Victor R. L. J. Bloemendal ◽  
Daan Sondag ◽  
Hidde Elferink ◽  
Thomas J. Boltje ◽  
Jan. C. M. van Hest ◽  
...  
Keyword(s):  
Late Stage ◽  
Cross Coupling ◽  
Modular Approach ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2009-2018
Author(s):  
Jan-Hendrik Lamm ◽  
Philipp Niermeier ◽  
Leif Körte ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Building Block ◽  
High Resolution Mass Spectrometry ◽  
Cross Coupling ◽  
Easy Access ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Resolution Mass

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

scholarly journals Crystal structures of three 4-substituted-2,2′-bipyridines synthesized by Sonogashira and Suzuki–Miyaura cross-coupling reactions

2017 ◽  
Vol 73 (4) ◽  
pp. 610-615
Author(s):  
Thuy Luong Thi Thu ◽  
Ngan Nguyen Bich ◽  
Hien Nguyen ◽  
Luc Van Meervelt
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Acta Cryst ◽  
X Ray ◽  
Π Interactions ◽  
Cross Coupling Reactions ◽  
Synthetic Routes ◽  
Solvent Molecules ◽  
The Given ◽  
Crystal Packings

Facile synthetic routes for three 4-substituted 2,2′-bipyridine derivatives, 4-[2-(4-methylphenyl)ethynyl]-2,2′-bipyridine, C19H14N2, (I), 4-[2-(pyridin-3-yl)ethynyl]-2,2′-bipyridine, C17H11N3, (II), and 4-(indol-4-yl)-2,2′-bipyridine, C18H13N3, (III),viaSonogashira and Suzuki–Miyaura cross-coupling reactions, respectively, are described. As indicated by X-ray analysis, the 2,2′-bipyridine core, the ethylene linkage and the substituents of (I) and (II) are almost planar [dihedral angles between the two ring systems: 8.98 (5) and 9.90 (6)° for the two molecules of (I) in the asymmetric unit and 2.66 (14)° for (II)], allowing π-conjugation. On the contrary, in (III), the indole substituent ring is rotated significantly out of the bipyridine plane [dihedral angle = 55.82 (3)°], due to steric hindrance. The crystal packings of (I) and (II) are dominated by π–π interactions, resulting in layers of molecules parallel to (30-2) in (I) and columns of molecules along theaaxis in (II). The packing of (III) exhibits zigzag chains of molecules along thecaxis interacting through N—H...N hydrogen bonds and π–π interactions. The contributions of unknown disordered solvent molecules to the diffraction intensities in (II) were removed with the SQUEEZE [Spek (2015).Acta Cryst.C71, 9–18] algorithm ofPLATON. The given chemical formula and other crystal data do not take into account these solvent molecules.

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.

Synthesis and structural characterization of substituted phenols with a m-terphenyl backbone 2,4,6-R3C6H2OH (R=2,4,6-Me3C6H2, Me5C6)

2015 ◽  
Vol 70 (1) ◽  
pp. 77-81 ◽  
Author(s):  
Atena B. Şolea ◽  
Marian Olaru ◽  
Cristian Silvestru ◽  
Ciprian I. Raţ
Keyword(s):  
Grignard Reagent ◽  
Cross Coupling ◽  
Molecular Structures ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
Substituted Phenols ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
C Nmr

AbstractSubstituted phenols with a m-terphenyl backbone 2,4,6-R3C6H2OH [R=2,4,6-Me3C6H2 (1), Me5C6 (2)] were synthesized using Kumada cross-coupling reactions between 2,4,6-I3C6H2OH and the corresponding Grignard reagent. Both compounds were structurally characterized in solution by 1H and 13C NMR spectroscopy and HRMS. The molecular structures of 1 and 2 were determined by single-crystal X-ray diffraction.

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