Diethanolamine Boronic Esters: Development of a Simple and Standard Process for Boronic Ester Synthesis

2020 ◽  
Vol 24 (9) ◽  
pp. 1683-1689
Author(s):  
Phillip A. Inglesby ◽  
Lauren R. Agnew ◽  
Holly L. Carter ◽  
Oliver T. Ring
Keyword(s):  
Ester Synthesis ◽  
Standard Process ◽  
Boronic Ester ◽  
Boronic Esters

scholarly journals Guest Inclusion Crystal structures of Macrocyclic Boronic Esters

2014 ◽  
Vol 70 (a1) ◽  
pp. C677-C677
Author(s):  
Ryosuke Toyoshima ◽  
Kotaro Fujii ◽  
Kohei Johmoto ◽  
Hidehiro Uekusa ◽  
Yuji Kikuchi ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Boronic Acid ◽  
Guest Molecule ◽  
Covalent Bond ◽  
Macrocyclic Compound ◽  
Channel Structure ◽  
Monoclinic System ◽  
One Dimensional ◽  
Boronic Ester ◽  
Boronic Esters

Macrocyclic compound has been attracting increasing attention because of their application for guest absorption and storage, guest selectivity, and reaction environment, which would utilize void space in the compound. Recently, such macrocyclic compound, boronic esters, has found to be formed as dynamic self-assembly of organic molecules through solvent dependent dynamic covalent bond formation between racemic polyol and planar 1,4-benzen(boronic acid)[1]. Thus, it is important to determine the crystal structure of the macrocyclic boronic esters with incorporated guest molecule to reveal the features of the compounds. In this study, structures of boronic ester of 1,4- naphthalene(boronic acid) (1) are presented and compared. The boronic ester with toluene guest molecule crystalized in monoclinic system, C2/c, Z=4, V=5099.7(6) Å3. As expected, toluene molecule was accommodated within a ring sandwiched by two naphthalene rings suggesting π-π interaction (ca. 3.6 Å separations). It is interesting that other structures of 1 with 1,4-dicyanobenzene, chloroform, and THF also have isomorphic structures to 1 with toluene. It clearly shows the guest inclusion ability of this boronic ester by weak intermolecular interactions. In the crystal structures, the boronic ester aligned along b-axis forming one-dimensional stacking with channel structure filled with guest molecules. Also, 1 with chloroform has a pseudo-polymorph phase (P21/c, V=5780.8(13) Å3) that has two additional chloroform molecules inside and outside of the ring; however, it also shows similar one-dimensional stacking structure with channel, implying this boronic ester has an easily stacking molecular shape. Although, the molecules have similar [2+2] ring structure, dihedral angle between two facing naphthalene rings is different in 1 with toluene, which is smaller as 14.10than 22 to 240in other structures. It may indicate a flexibility of the macrocyclic ring.

scholarly journals Chemoselective Boronic Ester Synthesis by Controlled Speciation

2014 ◽  
Vol 126 (45) ◽  
pp. 12273-12276 ◽  
Author(s):  
James W. B. Fyfe ◽  
Ciaran P. Seath ◽  
Allan J. B. Watson
Keyword(s):  
Ester Synthesis ◽  
Boronic Ester

ChemInform Abstract: Chemoselective Boronic Ester Synthesis by Controlled Speciation.

ChemInform ◽  
2015 ◽  
Vol 46 (15) ◽  
pp. no-no
Author(s):  
James W. B. Fyfe ◽  
Ciaran P. Seath ◽  
Allan J. B. Watson
Keyword(s):  
Ester Synthesis ◽  
Boronic Ester

scholarly journals The Synthesis of Biarylmonophosphonates via Palladium-Catalyzed Phosphonation, Iridium-Catalyzed C-H Borylation, Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling

2021 ◽  
Author(s):  
Simon Doherty ◽  
Julian G. Knight ◽  
Tina S. T. Tran ◽  
Hussam Y. Alharbi ◽  
Daniel O. Perry
Keyword(s):  
Cross Coupling ◽  
Statistical Mixture ◽  
Boronic Ester ◽  
Synthetic Procedure ◽  
Boronic Esters ◽  
Palladium Catalyzed ◽  
Nucleophilic Reagents ◽  
Sole Product

Abstract The iridium-catalyzed C-H borylation of diethyl phenylphosphonate results in nonselective mono and bisborylation to afford a near statistical mixture of 3-, 3,5- and 4-boryl substituted aryl phosphonates whereas 3-substituted aryl phosphonates undergo highly regioselective C-H borylation to afford the corresponding meta-phosphonate substituted arylboronic esters as the sole product; the resulting boronic esters were used as nucleophilic reagents in a subsequent palladium-catalyzed Suzuki–Miyaura cross-coupling to generate a range of biarylmonophosphonates. Gratifyingly, the Suzuki–Miyaura cross-coupling can be conducted without purifying the boronic ester which greatly simplifies the synthetic procedure. Graphical Abstract

Thermally healable and reprocessable polymethacrylate networks based on diol-mediated metathesis of 6-membered boronic esters

2020 ◽  
Vol 11 (11) ◽  
pp. 1860-1870 ◽  
Author(s):  
Yue Yang ◽  
Fu-Sheng Du ◽  
Zi-Chen Li
Keyword(s):  
Mechanical Properties ◽  
Dynamic Behaviors ◽  
Boronic Ester ◽  
Boronic Esters ◽  
Ester Linkage

We demonstrate the thermally repairable and reprocessable poly(methacrylate) networks crosslinked by boronic ester linkage, the dynamic behaviors and mechanical properties of which could be finely tuned by the pendent diols.

scholarly journals Assembly of synthetic Aβ miniamyloids on polyol templates

2015 ◽  
Vol 11 ◽  
pp. 2646-2653 ◽  
Author(s):  
Sebastian Nils Fischer ◽  
Armin Geyer
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Boronic Acids ◽  
Relative Orientation ◽  
Aβ Peptide ◽  
Aβ Peptides ◽  
Boronic Ester ◽  
Boronic Esters

Covalent dynamic chemistry is used to mimic the first steps of the highly cooperative fibril formation of Aβ peptides. For that purpose, Aβ peptide pentapeptide boronic acids 1 and 2 were synthesized by solid-phase peptide synthesis and studied in esterification experiments with polyhydroxylated templates. The bis-hydroxylated dipeptide Hot=Tap serves as a template of adjustable degree of oligomerization which spontaneously forms boronic esters with peptides of type 1 and 2. Nuclear magnetic resonance can differentiate between regioisomeric boronic esters and identifies preferred sites of esterification on the dimeric template 9. 2-Formylphenylboronic acid (14) is used to link the parent pentapeptide Leu-Val-Phe-Phe-Ala to the template 16 to obtain threefold boronic ester 17. The miniamyloid 17 assembles from seven components by imine and boronic ester bonds between the peptides and the template. The relative orientation and spacing of the peptides mimic the assembly of peptides in Alzheimer β-amyloids.

scholarly journals Complex Boron-Containing Molecules through a 1,2-Metalate Rearrangement/anti-S N 2′ Elimination/Cycloaddition Reaction Sequence

Synlett ◽  
2018 ◽  
Vol 30 (04) ◽  
pp. 449-453 ◽  
Author(s):  
Chloe Tillin ◽  
Raphael Bigler ◽  
Renata Calo-Lapido ◽  
Beatrice Collins ◽  
Adam Noble ◽  
...  
Keyword(s):  
Three Dimensional ◽  
Cycloaddition Reaction ◽  
Molecular Structures ◽  
Cycloaddition Reactions ◽  
Reaction Sequence ◽  
Boronic Ester ◽  
Boronic Esters ◽  
Three Component Coupling

The three-component coupling of benzylamines, boronic esters, and 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione (PTAD) is reported. The boronate complex formed from an ortho-lithiated benzylamine and a boronic ester undergoes a stereospecific 1,2-metalate rearrangement/anti-S N 2′ elimination in the presence of an N-activator to provide a dearomatized tertiary boronic ester. Interception of this dearomatized intermediate with a dienophile leads to stereopredictable cycloaddition reactions to generate highly complex three-dimensional boron-containing molecular structures. When enantioenriched α-methyl-substituted benzylamines are employed, the corresponding cycloaddition adducts are formed with excellent enantiospecificities.

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