Iridium-bipyridine periodic mesoporous organosilica catalyzed direct C-H borylation using a pinacolborane

Dalton Transactions : an International Journal of Inorganic Chemistry
Yoshifumi Maegawa, Shinji Inagaki

Abstract

Heterogeneous catalysis for direct C-H borylation of arenes and heteroarenes in the combination of iridium (Ir) complex fixed on periodic mesoporous organosilica containing bipyridine ligands within the framework (Ir-BPy-PMO) and pinacolborane (HBpin) is reported. Ir-BPy-PMO showed higher catalytic activity toward the borylation of benzene with inexpensive HBpin compared to expensive bis(pinacolato)diboron (B2pin2). The precatalyst could be handled without the use of a glove box. The catalyst was easily recovered from reaction mixtures by simple filtration under air. The recovered catalyst still showed good catalytic activity for at least three more times for the borylation of benzene. A variety of arenes and heteroarenes were successfully borylated with high boron efficiency by Ir-BPy-PMO using HBpin, whereas almost no activity was observed for borylation of some heteroarenes with B2pin2. The system using Ir-BPy-PMO and HBpin was also utilized in syntheses of multi-boronated thiophene-based building blocks containing ladder-, acenefused-, and fused-thiophene skeletons. The combination of a stable and reusable solid catalyst and inexpensive HBpin is expected to be superior to conventional approaches for the development of indus...Continue Reading

References

Mar 18, 2004·Journal of the American Chemical Society·Beng S OngSandra Gardner
Mar 21, 2006·Nature Materials·Iain McCullochMichael F Toney
Jul 13, 2006·Journal of the American Chemical Society·Hakan UstaTobin J Marks
Dec 7, 2006·Journal of the American Chemical Society·Sulagna PaulMilton R Smith
Mar 17, 2007·Journal of the American Chemical Society·Hualong PanGu Xu
Apr 9, 2009·Journal of the American Chemical Society·Soichiro KawamoritaMasaya Sawamura
Sep 30, 2009·Chemical Reviews·Yen-Ju ChengChain-Shu Hsu
Dec 24, 2009·Chemical Reviews·Ibraheem A I MkhalidJohn F Hartwig
Feb 28, 2014·Journal of the American Chemical Society·Minoru WakiShinji Inagaki

❮ Previous
Next ❯

Citations

Aug 28, 2015·Angewandte Chemie·Norihiro Mizoshita, Shinji Inagaki
Feb 13, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yuki NaganawaYumiko Nakajima
May 16, 2019·Angewandte Chemie·Sebastian LeubnerNorbert Stock
May 10, 2016·Physical Chemistry Chemical Physics : PCCP·Indre ThielChristophe Copéret
Oct 2, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Marek ČubiňákTomáš Tobrman
Apr 12, 2020·International Journal of Molecular Sciences·Chia-Hui LinChia-Hung Lee
Dec 6, 2017·Angewandte Chemie·Tobias GenschFrank Glorius
Nov 10, 2020·IScience·Ranjith Kumar KankalaAi-Zheng Chen
Apr 27, 2018·The Journal of Organic Chemistry·Shuhei NishinagaYasushi Nishihara
Dec 11, 2021·The Journal of Organic Chemistry·Chathurika R K JayasundaraRobert E Maleczka

❮ 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.