A set of diboryldiborenes are prepared by the mild, catalyst-free, room-temperature diboration of the B-B triple bonds of doubly base-stabilized diborynes. Two of the product diboryldiborenes are found to be air- and water-stable in the solid state, an effect that is attributed to their high crystallinity and extreme insolubility in a wide range of solvents.
Download full-text PDF |
Source |
|---|---|
| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6713863 | PMC |
| http://dx.doi.org/10.1039/c9sc02544h | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Platinum-Catalyzed Regio- and Enantioselective Diboration of Unactivated Alkenes with (pin)B-B(dan).
Angew Chem Int Ed Engl
August 2024
School of Chemistry, University of Bristol, Cantock's Close, BS8 1TS, Bristol, UK.
Asymmetric diboration of terminal alkenes is well established, and subsequent selective functionalization of the less hindered primary boronic ester is commonly achieved. Conversely, selective functionalization of the sterically less accessible secondary boronic ester remains challenging. An alternative way to control chemoselective functionalization of bis(boron) compounds is by engendering different Lewis acidity to the two boryl moieties, since reactivity would then be dictated by Lewis acidity instead of sterics.
View Article and Find Full Text PDFMechanistic Insights into the Metal-Free Deoxygenative Borylation of Ketones and Aldehydes with Bis(catecholato)diborane.
Chemistry
March 2023
Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023, P. R. China.
The mechanisms of direct deoxygenative borylation of acetone and benzaldehyde with bis(catecholato)diborane (B cat ) in the solvent N,N-dimethylacetamide (DMA) are investigated through detailed density functional theory calculations. These calculations show that the isomer 1,2-B cat in situ generated from 1,1-B cat induced by DMA is the reactive boron intermediate for the reactions. The addition of the B-B bond of 1,2-B cat to the C=O bond of acetone or benzaldehyde via a concerted [2σ+2π]-cycloaddition-like transition state is the rate-limiting step for both the triboration reaction of acetone and the monoboration reaction of benzaldehyde.
View Article and Find Full Text PDFDiboration of alkenes and alkynes with a carborane-fused four-membered boracycle bearing an electron-precise B-B bond.
Dalton Trans
November 2021
Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, N. T., Hong Kong, China.
Small ring compounds are fascinating molecules and have been used as valuable compounds in organic synthesis. In this study, a carborane-fused four-membered boracycle bearing an electron precise B-B bond, 1,2-[BBrSMe]--CBH, was synthesized the reaction of 1,2-Li--carborane with BBr(SMe). This novel boracycle can be used as a "strain-release" compound to achieve diboration of alkenes and alkynes, leading to the generation of ring-expansion products.
View Article and Find Full Text PDFMechanistic insights into the dearomative diborylation of pyrazines: a radical or non-radical process?
Dalton Trans
May 2021
Key Laboratory of Mesoscopic Chemistry of Ministry of Education, Institute of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China.
The mechanisms of the dearomative diborylation of pyrazines were investigated via a combination of density functional theory (DFT) calculations and experimental studies. DFT calculations revealed that a non-radical mechanism involving two successive [3,3]-σ-rearrangement-type processes is responsible for the diborylation of pyrazine with bis(pinacolato)diboron (B2pin2). However, this non-radical process is highly unfavorable for the diborylation reaction of sterically hindered pyrazine (2,3-dimethylpyrazine).
View Article and Find Full Text PDFMild synthesis of diboryldiborenes by diboration of B-B triple bonds.
Chem Sci
August 2019
Institut für Anorganische Chemie , Julius-Maximilians-Universität Würzburg, Am Hubland , 97074 Würzburg , Germany . Email:
A set of diboryldiborenes are prepared by the mild, catalyst-free, room-temperature diboration of the B-B triple bonds of doubly base-stabilized diborynes. Two of the product diboryldiborenes are found to be air- and water-stable in the solid state, an effect that is attributed to their high crystallinity and extreme insolubility in a wide range of solvents.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!