Flow‐Chemistry‐Enabled Synthesis of 5‐Diethylboryl‐2, 3′‐bipyridine and Its Self‐Assembly Dynamics

S Wakabayashi, M Takumi, S Kamio… - … A European Journal, 2023 - Wiley Online Library
Diethylboryl‐2, 3′‐bipyridine (1), which is inaccessible by conventional batch methods,
was synthesized by using a flow microreactor. Compound 1 was obtained as an equilibrium …

Self-Assembly of 3-[4 '-(Diethylboryl) phenyl] pyridine and 3-[3 '-(Diethylboryl) phenyl] pyridine: Synthesis, Structural Features, and Stability in Solution

S Wakabayashi, Y Sugihara, K Takakura… - The Journal of …, 1999 - ACS Publications
The self-assembly of 3-[4 '-(diethylboryl) phenyl] pyridine (3) and 3-[3 '-(diethylboryl) phenyl]
pyridine (4) was investigated by 1H and 11B NMR spectroscopies and vapor pressure …

3-(dimethylboryl) pyridine: Synthesis, structure, and remarkable steric effects in scrambling reactions

S Wakabayashi, S Imamura, Y Sugihara… - The Journal of …, 2008 - ACS Publications
A facile method for the synthesis of 3-(dimethylboryl) pyridine (1a) is described. Compound
1a assembles into a rigid cyclic tetramer stabilized via intermolecular boron− nitrogen …

Self-Assembly and Exfoliation of a Molecular Solid Based on Cooperative B–N and Hydrogen Bonds

L Fornasari, R Mazzaro, E Boanini… - Crystal Growth & …, 2018 - ACS Publications
Herein we report that 4-pyridinylboronic acid (1) in the solid state self-assembles into
tetrameric macrocycles via B–N bond formation. The tetramers are linked via O–H··· O bonds …

A scalable synthesis of 5, 5′-dibromo-2, 2′-bipyridine and its stepwise functionalization via Stille couplings

DM D'souza, DA Leigh, M Papmeyer, SL Woltering - nature protocols, 2012 - nature.com
Abstract The synthesis of 5, 5′-dibromo-2, 2′-bipyridine and 5-bromo-2, 2′-bipyridine,
useful intermediates for elaboration into more complex ligands through metal-catalyzed …

Synthesis of biaryls having a piperidylmethyl group based on space integration of lithiation, borylation, and Suzuki–Miyaura coupling

Y Takahashi, Y Ashikari, M Takumi… - European Journal of …, 2020 - Wiley Online Library
In a flow microreactor, aryllithiums bearing a piperidylmethyl group were generated using
nBuLi by precise residence time control and effective temperature control, and then …

Spectroscopic and computational investigations of the thermodynamics of boronate ester and diazaborole self-assembly

AR Goldberg, BH Northrop - The Journal of organic chemistry, 2016 - ACS Publications
The solution phase self-assembly of boronate esters, diazaboroles, oxathiaboroles, and
dithiaboroles from the condensation of arylboronic acids with aromatic diol, diamine …

Supramolecular polymerization of benzene-1, 3, 5-tricarboxamide: a molecular dynamics simulation study

KK Bejagam, G Fiorin, ML Klein… - The Journal of …, 2014 - ACS Publications
Supramolecular polymerization in the family of benzene-1, 3, 5-tricarboxamide (BTA) has
been investigated using atomistic molecular dynamics (MD) simulations. Gas phase …

Synthesis of a drug-like focused library of trisubstituted pyrrolidines using integrated flow chemistry and batch methods

M Baumann, IR Baxendale, C Kuratli… - ACS Combinatorial …, 2011 - ACS Publications
A combination of flow and batch chemistries has been successfully applied to the assembly
of a series of trisubstituted drug-like pyrrolidines. This study demonstrates the efficient …

Tetraborylation of p-Benzynes Generated by the Masamune–Bergman Cyclization through Reaction Design Based on the Reaction Path Network

S Nakatsuka, S Akiyama, Y Harabuchi, S Maeda… - JACS Au, 2024 - ACS Publications
Designing the reactant molecule of an initial reaction, based on quantum chemical pathway
exploration, enabled us to access a new reaction, ie, the tetraborylation reaction of p …