From 1,2-difunctionalisation to cyanide-transfer cascades - Pd-catalysed cyanosulfenylation of internal (oligo)alkynes.

Chemical Science
Marcel BürgerDaniel B Werz

Abstract

Internal alkynes substituted by aliphatic or aromatic moieties or by heteroatoms were converted into sulphur-substituted acrylonitrile derivatives. Key is the use of Pd catalysis, which allows the addition of aromatic and aliphatic thiocyanates in an intra- and intermolecular manner. Substrates with several alkyne units underwent further carbopalladation steps after the initial thiopalladation step, thus generating in a cascade-like fashion an oligoene unit with sulphur at one terminus and the cyano group at the other.

References

Feb 1, 1996·Chemical Reviews·Lutz F. Tietze
Jun 6, 2003·Journal of the American Chemical Society·Michinori SuginomeMasahiro Murakami
Oct 28, 2004·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Feb 14, 2007·Journal of the American Chemical Society·Yoshiaki NakaoTamejiro Hiyama
Jul 17, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Meiyan WangZhijian Wu
Jan 26, 2010·Nature Chemical Biology·Markus LeibelingDaniel B Werz
Jul 9, 2010·Journal of the American Chemical Society·Yasuhiro HirataSensuke Ogoshi
Jan 27, 2011·Journal of the American Chemical Society·Stephen G Newman, Mark Lautens
Mar 23, 2011·Organic Letters·Naveen R RondlaChristopher J Douglas
Apr 3, 2012·Journal of the American Chemical Society·Dennis C KoesterYoshiaki Nakao
May 25, 2012·Chemical Communications : Chem Comm·Kanniyappan ParthasarathyChien-Hong Cheng
Feb 14, 2013·Angewandte Chemie·Lutz F TietzeDietmar Stalke
Dec 7, 2013·Angewandte Chemie·Jan WallbaumDaniel B Werz
Mar 4, 2014·Journal of the American Chemical Society·Yosuke MiyazakiYoshiaki Nakao
Sep 5, 2015·Angewandte Chemie·Shermin S GohEdward A Anderson
Feb 19, 2016·Journal of the American Chemical Society·Xi Wang, Armido Studer
May 3, 2016·Angewandte Chemie·Sarah BlouinJean Suffert
Sep 27, 2016·Chemistry : a European Journal·Alexander Düfert, Daniel B Werz
Aug 18, 2017·Angewandte Chemie·Alejandro G BarradoManuel Alcarazo
Apr 4, 2018·The Journal of Organic Chemistry·Shinya HigashimaeAkiya Ogawa
Jan 9, 2019·Chemistry : a European Journal·Phillip D G GreenwoodJerome Waser
Feb 28, 2019·Angewandte Chemie·Yong Ho Lee, Bill Morandi
Jun 12, 2019·Chemical Reviews·Katerina M Korch, Donald A Watson

❮ Previous
Next ❯

Citations

Jun 9, 2020·Angewandte Chemie·Yuanzhe ZhangShih-Yuan Liu
Jul 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mickael ChouryMihaela Gulea
Feb 16, 2021·Chemical Communications : Chem Comm·Sandeep PimparkarDebabrata Maiti
Mar 12, 2021·The Journal of Organic Chemistry·Haopeng WuFu-Xue Chen
Sep 30, 2021·Journal of the American Chemical Society·Marcel BürgerDaniel B Werz
Oct 7, 2021·Chemistry : a European Journal·Finn J GeffersDaniel B Werz

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

Software Mentioned

XantPhos

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.

Related Papers

Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]
Tetsuya SatohMasahiro Miura
Accounts of Chemical Research
Igor V Alabugin, Edgar Gonzalez-Rodriguez
© 2021 Meta ULC. All rights reserved