Generation of an N→B Ladder-type Structure by Regioselective Hydroboration of an Alkenyl-Functionalized Quaterpyridine

Chemistry : a European Journal
Markus GrandlFrank Pammer

Abstract

An unusual reactivity of 2-(1-alkenyl)-pyridines towards hydroboration with 9H-borabicyclo[3.3.1]nonane (9H-BBN) has been employed to selectively introduce two borane groups into a conjugated quaterpyridine. Quantitative conversion of the substrate was observed with exclusive regioselectivity. A molecular structure that allows intramolecular N→B coordination was generated. The effect of the ladder formation on the molecular structure and the electronic properties of the conjugated system have been investigated. The synthetic strategy demonstrated herein offers a facile access to N→B ladder-type structures from readily available substrates, and allows to simultaneously introduce several boron centers under mild conditions.

References

Aug 1, 1987·Physical Review A: General Physics·W N Hansen, G J Hansen
Jan 19, 2002·The Journal of Organic Chemistry·Peter F H SchwabJosef Michl
Aug 31, 2002·Angewandte Chemie·Christopher D Entwistle, Todd B Marder
Feb 1, 2007·Chemical Communications : Chem Comm·Junro YoshinoTakayuki Kawashima
Jun 15, 2010·Chemical Reviews·Casey R WadeFrançois P Gabbaï
Oct 16, 2010·Organic Letters·Stephen K MurphySuning Wang
Nov 26, 2010·The Journal of Organic Chemistry·Naoki IshidaMasahiro Murakami
Mar 4, 2011·Journal of the American Chemical Society·Alexander HübnerMatthias Wagner
Mar 8, 2011·Journal of the American Chemical Society·Gregory C Welch, Guillermo C Bazan
May 14, 2011·Macromolecular Rapid Communications·Sebastiano CataldoBruno Pignataro
May 2, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Andreas LorbachMatthias Wagner
Jun 22, 2012·Organic Letters·David CurielPedro Molina
Aug 10, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Ying-Li RaoSuning Wang
Apr 9, 2013·Angewandte Chemie·Jia-Sheng LuSuning Wang
Jan 22, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·George Rajendra Kumar, Pakkirisamy Thilagar
Oct 21, 2015·Angewandte Chemie·Suning WangZheng-Hong Lu
Oct 29, 2015·Physical Chemistry Chemical Physics : PCCP·George Rajendra KumarPakkirisamy Thilagar

❮ Previous
Next ❯

Citations

Apr 18, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Di WuFrançois Mathey
Jun 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Frank PammerAndreas Orthaber
Apr 30, 2020·Chemistry : a European Journal·Zi-Di YuJian Pei
Jul 28, 2016·Chemistry : a European Journal·Daniel L CrossleyMichael J Ingleson
Dec 15, 2016·Chemical Reviews·Adam GorczyńskiArtur R Stefankiewicz
Oct 7, 2021·The Journal of Organic Chemistry·Jonas D W SchepperFrank Pammer

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.