Double-Fold Ortho and Remote C-H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL

Organic Letters
Ranjana BishtBuddhadeb Chattopadhyay

Abstract

A double-fold ortho and remote C-H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C-H activation processes, respectively. While B2eg2 (eg = ethylene glycolate) directs the C-H activation at ortho positions, a combination of HBpin and B2pin2 activates remote C-H bonds. The strategy was combined with Suzuki arylation as a one-pot protocol for the rapid synthesis of BINOL derivatives with retention of chirality.

References

Oct 24, 2001·The Journal of Organic Chemistry·Klaus B. SimonsenKarl Anker Jørgensen
Aug 14, 2003·Chemical Reviews·Yu ChenAndrei K Yudin
Mar 10, 2005·Chemical Reviews·Jean Michel Brunel
Jul 27, 2006·Journal of the American Chemical Society·Daisuke Nakashima, Hisashi Yamamoto
Nov 7, 2007·Chemical Reviews·Takahiko Akiyama
Dec 13, 2007·Chemical Reviews·Takuya Hashimoto, Keiji Maruoka
Dec 13, 2007·Chemical Reviews·Abigail G Doyle, Eric N Jacobsen
Aug 14, 2008·Chemical Reviews·M Mar Díaz-Requejo, Pedro J Pérez
Nov 4, 2009·Chemical Communications : Chem Comm·Cathleen M CruddenChristopher J Lata
Dec 22, 2009·Journal of the American Chemical Society·Bin XiaoLei Liu
Dec 24, 2009·Chemical Reviews·Ibraheem A I MkhalidJohn F Hartwig
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
May 27, 2011·Chemical Society Reviews·Magnus RuepingIuliana Atodiresei
Mar 2, 2013·Angewandte Chemie·Seiji Shirakawa, Keiji Maruoka
Feb 21, 2014·Chemical Society Reviews·A RosJ M Lassaletta
Aug 11, 2015·Journal of the American Chemical Society·Yu FengPhil S Baran
Nov 14, 2015·Journal of the American Chemical Society·John F Hartwig
Dec 23, 2015·Journal of the American Chemical Society·Ranjana Bisht, Buddhadeb Chattopadhyay
Apr 14, 2016·Chemical Society Reviews·T GenschJ Wencel-Delord
Dec 14, 2016·Journal of the American Chemical Society·Sachin NaruteDoron Pappo
Dec 31, 2016·Angewandte Chemie·Hong Liang LiMotomu Kanai
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong
May 26, 2017·Journal of the American Chemical Society·Md Emdadul HoqueBuddhadeb Chattopadhyay

❮ 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.