A metal-free direct C (sp3 )-H cyanation reaction with cyanobenziodoxolones

Organic & Biomolecular Chemistry
Ming-Xue SunSuo-Jiang Zhang

Abstract

A metal-free protocol of direct C(sp3)-H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.

References

Oct 25, 2001·The Journal of Organic Chemistry·Terry V. Hughes, Michael P. Cava
Aug 13, 2004·Angewandte Chemie·Michael North
Aug 12, 2009·Chemical Communications : Chem Comm·Wei Han, Armin R Ofial
Mar 24, 2010·Chemistry : a European Journal·Pazhamalai AnbarasanMatthias Beller
Sep 2, 2010·Journal of Medicinal Chemistry·Fraser F FlemingBrian C Shook
Dec 15, 2010·Chemical Communications : Chem Comm·Yan ZhangChengjian Zhu
Oct 14, 2011·Organic Letters·Shin KamijoMasayuki Inoue
Nov 2, 2011·Chemical Communications : Chem Comm·Magnus RuepingRené M Koenigs
Jan 10, 2013·Journal of the American Chemical Society·Maxim O Ratnikov, Michael P Doyle
Jan 29, 2013·Angewandte Chemie·Xinxin ShaoQilong Shen
Mar 30, 2013·Journal of the American Chemical Society·Qing-Hai DengLutz H Gade
Jul 5, 2013·Journal of the American Chemical Society·Tian-Jun GongYao Fu
Dec 18, 2013·Organic Letters·Yu-Tao HeYong-Min Liang
Feb 1, 2014·Angewandte Chemie·Alexander Nierth, Michael A Marletta
Aug 27, 2014·Chemical Communications : Chem Comm·Alexandre Pradal, Gwilherm Evano
Sep 16, 2014·Chemistry : a European Journal·Nicola Otto, Till Opatz
Oct 21, 2014·Chemical Communications : Chem Comm·Juan LiJingsong You
Nov 20, 2014·Organic & Biomolecular Chemistry·Yao-Feng WangFu-Xue Chen
Dec 19, 2014·Chemistry : a European Journal·Reto FreiJerome Waser
Jul 16, 2016·Angewandte Chemie·Kensuke KiyokawaSatoshi Minakata
Dec 6, 2016·Chemistry : a European Journal·Jia-Shen QiuFu-Xue Chen
Feb 25, 2017·Angewandte Chemie·Ángel L Fuentes de ArribaDarren J Dixon
Jun 22, 2017·Accounts of Chemical Research·Xi Wang, Armido Studer
Sep 21, 2017·Angewandte Chemie·Satobhisha MukherjeeFrank Glorius

❮ Previous
Next ❯

Citations

Feb 14, 2020·Organic & Biomolecular Chemistry·Arindam MaityAlakesh Bisai
Jul 24, 2020·Chemical Communications : Chem Comm·William K WeigelDavid B C Martin
Oct 1, 2020·Chemical Communications : Chem Comm·Shuai LiuYannick Landais
May 13, 2021·Chemistry : a European Journal·Eliott Le DuJerome Waser
Jul 7, 2021·Organic Letters·Kunsoon KimSoon Hyeok Hong
Sep 18, 2018·The Journal of Organic Chemistry·Sebastien AlazetJerome Waser
Oct 16, 2021·Organic & Biomolecular Chemistry·William K WeigelDavid B C Martin

❮ 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.