Control of the reversibility during boronic ester formation: application to the construction of ferrocene dimers and trimers

2017 ◽  
Vol 46 (7) ◽  
pp. 2370-2376 ◽  
Author(s):  
Kosuke Ono ◽  
Yohei Tohyama ◽  
Tatsuhiro Uchikura ◽  
Yuji Kikuchi ◽  
Kotaro Fujii ◽  
...  
Keyword(s):  
Aprotic Solvents ◽  
Boronic Ester ◽  
Ester Formation ◽  
Boronic Esters ◽  
Neutral Conditions

Equilibration of boronic esters during boronic ester formation was controlled using protic or aprotic solvents under neutral conditions.

RNA-directed off/on switch of RNase H activity using boronic ester formation

2017 ◽  
Vol 15 (38) ◽  
pp. 8204-8210 ◽  
Author(s):  
Maëva Reverte ◽  
Ivan Barvik ◽  
Jean-Jacques Vasseur ◽  
Michael Smietana
Keyword(s):  
Boronic Acid ◽  
Rnase H ◽  
Boronic Ester ◽  
Ester Formation

A new concept to modulate RNase H activity is presented based on the boronic acid/boronate switch.

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.

Transition metal- and photo-free radical borylation of alkyl bromides and iodides by silane

2021 ◽  
Author(s):  
Beiqi Sun ◽  
Sihan Zheng ◽  
Fanyang Mo
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Alkyl Bromides ◽  
Boronic Esters ◽  
Neutral Conditions

We report an operationally simple and neutral conditions for borylation of alkyl bromides and iodides to alkyl boronic esters under transition metal- and photo-free conditions. A series of substrates with...

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

Dynamic and Programmable DNA-Templated Boronic Ester Formation

2011 ◽  
Vol 50 (18) ◽  
pp. 4193-4196 ◽  
Author(s):  
Anthony R. Martin ◽  
Ivan Barvik ◽  
Delphine Luvino ◽  
Michael Smietana ◽  
Jean-Jacques Vasseur
Keyword(s):  
Boronic Ester ◽  
Ester Formation

scholarly journals Interdependent Dynamic Nitroaldol and Boronic Ester Reactions for Complex Dynamers of Different Topologies

2021 ◽  
Author(s):  
Antanas Karalius ◽  
Yunchuan Qi ◽  
Mubarak Ayinla ◽  
Zoltan Szabo ◽  
Olof Ramstrom
Keyword(s):  
Dynamic Systems ◽  
Main Chain ◽  
Building Blocks ◽  
Boronic Acids ◽  
Complex Dynamic ◽  
Complex Dynamic Systems ◽  
Boronic Ester ◽  
Ester Formation ◽  
Nitroaldol Reaction ◽  
Hydrolysis Of

Complex dynamic systems displaying interdependency between nitroaldol and boronic ester reactions have been demonstrated. Nitroalkane-1,3-diols, generated by the nitroaldol reaction, were susceptible to ester formation with different boronic acids in aprotic solvents, whereas hydrolysis of the esters occurred in the presence of water. The boronic ester formation led to significant stabilization of the nitroaldol adducts under basic conditions. The use of bifunctional building blocks was furthermore established, allowing for main chain nitroaldol-boronate dynamers as well as complex network dynamers with distinct topologies. The shape and rigidity of the resulting dynamers showed an apparent dependency on the configuration of the boronic acids.

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.

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