(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors.

Chemistry : a European Journal
Kensuke SuzukiMakoto Yasuda

Abstract

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radical initiator to give the corresponding organic boron compounds. Radical clock experiments and computational studies have provided insights into the mechanism of the homolytic substitution (SH 2) of the borylstannanes with alkyl radical intermediates. DFT calculation disclosed that the phenylenediamino structure lowered the LUMO level including the vacant p-orbital on the boron atom to enhance the reactivity to alkyl radicals in SH 2. Moreover, C(sp3 )-H borylation of THF was accomplished using the triplet state of xanthone.

References

Feb 14, 2002·Chemical Reviews·C Ollivier, P Renaud
May 29, 2007·Chemical Reviews·Maurizio FagnoniAngelo Albini
Dec 24, 2009·Chemical Reviews·Ibraheem A I MkhalidJohn F Hartwig
Dec 3, 2016·Organic & Biomolecular Chemistry·K KubotaH Ito
Apr 12, 2017·Chemical Communications : Chem Comm·Christopher Sandford, Varinder K Aggarwal
May 6, 2017·Chemical Communications : Chem Comm·Ryohei UematsuSatoshi Maeda
Jun 18, 2017·Science·Alexander FawcettVarinder K Aggarwal
Jun 24, 2017·Chemical Reviews·Hong YiAiwen Lei
Aug 10, 2018·Journal of the American Chemical Society·Jingjing WuVarinder K Aggarwal
Apr 18, 2017·European Journal of Organic Chemistry·Luca Capaldo, Davide Ravelli
Sep 27, 2018·Angewandte Chemie·Jiefeng HuZhuangzhi Shi
Oct 18, 2018·Angewandte Chemie·Ying ChengArmido Studer
May 3, 2019·Angewandte Chemie·Florian W Friese, Armido Studer
Oct 16, 2019·Angewandte Chemie·Jingjing WuVarinder K Aggarwal
Feb 6, 2020·Chemical Science·Florian W Friese, Armido Studer
Apr 16, 2020·Chem·Xin MuAlexander M Spokoyny
Jul 1, 2020·Chemical Reviews·Minyan Wang, Zhuangzhi Shi
Aug 5, 2020·Chemical Communications : Chem Comm·Guobin MaHegui Gong
Aug 26, 2020·Angewandte Chemie·Qiang ZhangYi Pan
Oct 30, 2020·Nature·Chao ShuVarinder K Aggarwal

❮ Previous
Next ❯

Citations

Sep 10, 2021·Chemistry : a European Journal·Dmitriy M VolochnyukOleksandr O Grygorenko

❮ 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.