Synthesis of pyridines from ketoximes and terminal alkynes via C-H bond functionalization.

The Journal of Organic Chemistry
Rhia M MartinJonathan A Ellman

Abstract

An expedient one-pot rhodium catalyzed C-H bond functionalization/electrocyclization/dehydration procedure has been developed for the synthesis of highly substituted pyridine derivatives from terminal alkynes and α,β-unsaturated ketoximes. The use of electron-deficient phosphite ligands is important to suppress dimerization of the terminal alkynes to enynes.

References

Sep 18, 2001·The Journal of Organic Chemistry·C G HartungM Beller
May 2, 2002·Journal of the American Chemical Society·Tamotsu TakahashiMartin Kotora
Sep 11, 2003·Chemical Reviews·Jesús A Varela, Carlos Saá
Nov 30, 2004·Chemical Communications : Chem Comm·Sensuke OgoshiHideo Kurosawa
Apr 7, 2005·Journal of the American Chemical Society·Michael M McCormickJanis Louie
May 26, 2005·Journal of the American Chemical Society·Ryoichi TanakaHirokazu Urabe
Apr 6, 2006·Journal of the American Chemical Society·Mohammad Movassaghi, Matthew D Hill
Jun 10, 2006·Organic & Biomolecular Chemistry·John S CareyMike T Williams
Nov 10, 2006·Chemical Reviews·Gilson Zeni, Richard C Larock
Mar 17, 2007·Organic Letters·Barry M Trost, Alicia C Gutierrez
Aug 1, 2007·Journal of the American Chemical Society·Mohammad MovassaghiOmar K Ahmad
Jan 19, 2008·Angewandte Chemie·André M BeaucheminSerge I Gorelsky
Feb 28, 2008·Journal of the American Chemical Society·Denise A ColbyJonathan A Ellman
Jul 25, 2009·Organic Letters·Michel ObringerFrançoise Colobert
Oct 12, 2011·Chemical Communications : Chem Comm·Todd K Hyster, Tomislav Rovis

❮ Previous
Next ❯

Citations

Dec 19, 2012·Journal of the American Chemical Society·Jamie M Neely, Tomislav Rovis
Feb 13, 2013·Journal of the American Chemical Society·Michael A IschayJonathan A Ellman
Feb 9, 2016·Journal of the American Chemical Society·Wei-Jun KongJin-Quan Yu
Nov 5, 2016·The Journal of Organic Chemistry·Justin A HilfScott D Rychnovsky
Apr 8, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·María Vicky Corona-GonzálezVirginia Montiel-Palma
Feb 6, 2017·Organic & Biomolecular Chemistry·Hai-Bin Yang, Nicklas Selander
Nov 25, 2014·Chemical Society Reviews·Huawen HuangHuanfeng Jiang
Jan 5, 2016·Organic & Biomolecular Chemistry·Huawen HuangGuo-Jun Deng
Dec 7, 2017·Organic & Biomolecular Chemistry·Yujia XiaGuo-Jun Deng
Dec 6, 2018·Organic & Biomolecular Chemistry·Takeru Miyakoshi, Hiroyuki Konno
Feb 14, 2019·Organic & Biomolecular Chemistry·Yilmaz Kelgokmen, Metin Zora
Jun 23, 2016·Angewandte Chemie·Moisés Gulías, José Luis Mascareñas
Jun 19, 2013·Chemistry : a European Journal·Hao LiangZheng-Hui Guan
Dec 15, 2015·Beilstein Journal of Organic Chemistry·Dimitra KontokostaLaura L Anderson
Apr 10, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xian-Ying ShiChao-Jun Li
Jan 3, 2013·Chemistry : a European Journal·Fen XuBoshun Wan
May 27, 2021·Chemistry : a European Journal·Karunanidhi MuraliDebabrata Maiti
Nov 29, 2017·The Journal of Organic Chemistry·Anthony Y ChenHaiming Zhang
Jun 29, 2013·Organic Letters·Johannes LehmannRobert Britton
Mar 23, 2019·The Journal of Organic Chemistry·Raghuram GujjarappaChandi C Malakar

❮ 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.