Copper-catalyzed radical reaction of N-tosylhydrazones: stereoselective synthesis of (E)-vinyl sulfones

Organic Letters
Shuai MaoYong-Qiang Wang

Abstract

A new chemistry of hydrazines that is a copper-catalyzed radical reaction to synthesize vinyl sulfones from readily available N-tosylhydrazones has been described. The protocol provides a novel strategy for the synthesis of various vinyl sulfones including α, β-disubstituted ones and terminal ones. The advantages of the transformation include excellent E stereoselectivity, broad substrate scope, low cost of reagents, and convenient operation. A novel and efficient one-pot synthesis of alkynes from N-tosylhydrazones has been achieved. The studies provide important complementary approaches for the syntheses of vinyl sulfones and alkynes.

References

Apr 11, 2000·Accounts of Chemical Research·D EndersR Peters
Aug 22, 2001·Chemistry & Biology·A F Kisselev, A L Goldberg
Jan 31, 2003·Organic Letters·Mizio MatteucciMark Bradley
Apr 10, 2003·Chemical Reviews·Hélène LebelAndré B Charette
Jun 10, 2004·Chemical Reviews·Francisco AlonsoMiguel Yus
Jun 23, 2005·Journal of the American Chemical Society·Hongming LiLi Deng
Jul 8, 2005·Journal of Medicinal Chemistry·D Christopher MeadowsJacquelyn Gervay-Hague
Jan 4, 2007·Chemistry : a European Journal·José Marco-Contelles, Elena Soriano
Mar 10, 2007·Angewandte Chemie·Nicolas Marion, Steven P Nolan
Aug 19, 2007·Journal of the American Chemical Society·Mohammad N NoshiPhilip L Fuchs
Dec 20, 2007·Journal of Medicinal Chemistry·M V Ramana ReddyE Premkumar Reddy
Jan 12, 2008·Journal of the American Chemical Society·Cheng PengJianbo Wang
Jan 25, 2008·Nature·Huw M L Davies, James R Manning
May 8, 2009·Chemical Society Reviews·J B Sweeney
Sep 30, 2009·Chemical Reviews·Michael P DoyleLei Zhou
Oct 23, 2009·Chemical Society Reviews·Huw M L Davies, Justin R Denton
Oct 23, 2009·Chemical Society Reviews·Albert Padwa
Jan 22, 2010·Angewandte Chemie·Zhenhua ZhangJianbo Wang
Apr 27, 2010·Chemical Society Reviews·Erica JellemaBas de Bruin
Jun 15, 2010·European Journal of Medicinal Chemistry·Ana S NewtonMaria M M Santos
Jun 24, 2010·Nature Chemistry·Shou-Fei ZhuQi-Lin Zhou
Jul 26, 2011·Chemical Society Reviews·Zhihui Shao, Hongbin Zhang
Apr 28, 2012·Angewandte Chemie·José BarluengaCarlos Valdés
May 29, 2012·Angewandte Chemie·M Carmen Pérez-Aguilar, Carlos Valdés

❮ 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.