Trapping of Terminal Platinapolyynes by Copper(I) Catalyzed Click Cycloadditions; Probes of Labile Intermediates in Syntheses of Complexes with Extended sp Carbon Chains, and Crystallographic Studies.

Chemistry : a European Journal
Hashem AminiJohn A Gladysz

Abstract

The silylated hexatriynyl complex trans-(C6 F5 )(p-tol3 P)2 Pt(C≡C)3 SiEt3 (PtC6 TES) is converted in situ to PtC6 H (wet n-Bu4 N+ F- , THF) and cross coupled with the diyne H(C≡C)2 SiEt3 (HC4 TES; CuCl/TMEDA, O2 ) to give PtC10 TES (71 %). This sequence is repeated twice to afford PtC14 TES (65 %) and then PtC18 TES (27 %). An analogous series of reactions starting with PtC8 TES gives PtC12 TES (60 %), then PtC16 TES (43 %), and then PtC20 TES (17 %). Similar cross couplings with H(C≡C)2 Si(i-Pr)3 (HC4 TIPS) give PtC12 TIPS (68 %), PtC14 TIPS (68 %), and PtC16 TIPS (34 %). The trialkylsilyl species (up to PtC18 TES) are converted to 3+2 "click" cycloadducts or 1,4-disubstituted 1,2,3-triazoles trans-(C6 F5 )(p-tol3 P)2 Pt(C≡C)n-1 C=CHN(CH2 C6 H5 )N=N (29-92 % after workups). The most general procedure involves generating the terminal polyynes PtCx H (wet n-Bu4 N+ F- , THF) in the presence of benzyl azide in DMF and aqueous CuSO4 /ascorbic acid. All of the preceding complexes are crystallographically characterized and the structural and spectroscopic properties analyzed as a function of chain length. Two pseudopolymorphs of PtC20 TES are obtained, both of which feature molecules with parallel sp carbon chains in a pairwise head...Continue Reading

References

Feb 15, 2002·Chemistry : a European Journal·Thomas GibtnerAndreas Hirsch
Nov 13, 2003·Chemical Reviews·Slawomir Szafert, J A Gladysz
Feb 24, 2005·Journal of the American Chemical Society·Sara EislerRik R Tykwinski
Aug 4, 2006·The Journal of Physical Chemistry. a·Shujiang Yang, Miklos Kertesz
Nov 15, 2006·Chemical Reviews·Slawomir Szafert, J A Gladysz
Apr 3, 2007·Inorganic Chemistry·Wei-Zhong ChenTong Ren
May 7, 2008·Organic Letters·Jamie KendallRik R Tykwinski
Aug 14, 2008·Chemical Reviews·Morten Meldal, Christian Wenzel Tornøe
Feb 10, 2009·Journal of the American Chemical Society·Andrea LucottiRik R Tykwinski
Aug 12, 2009·Angewandte Chemie·Wesley A ChalifouxRik R Tykwinski
Oct 23, 2010·Nature Chemistry·Wesley A Chalifoux, Rik R Tykwinski
Nov 13, 2010·The Journal of Organic Chemistry·Thanh LuuRik R Tykwinski
Feb 19, 2013·Chemistry : a European Journal·Luis CasarrubiosMiguel A Sierra
Oct 8, 2013·ACS Nano·Mingjie LiuBoris I Yakobson
Dec 5, 2014·Journal of the American Chemical Society·Levon D MovsisyanHarry L Anderson
Jul 23, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Rik R Tykwinski
Oct 23, 2015·Chemistry : a European Journal·Bartłomiej PigulskiSławomir Szafert
Jan 14, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Natalia ZabarskaSven Rau
Jun 8, 2019·Chemistry : a European Journal·Mathis KreuzahlerGebhard Haberhauer
Oct 10, 2019·Organic & Biomolecular Chemistry·Sankaran RadhikaGopinathan Anilkumar
Jan 17, 2020·Current Opinion in Chemical Biology·Nicola J Farrer, Darren M Griffith
Sep 25, 2020·Nature Communications·Johannes ZirzlmeierHolger Frauenrath

❮ 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.

Related Papers

Cold Spring Harbor Protocols
International Journal of Bioinformatics Research and Applications
Mo-Li HuangWanwipa Vongsangnak
Tumour Biology : the Journal of the International Society for Oncodevelopmental Biology and Medicine
Yang YongbinJiao Manjing
© 2021 Meta ULC. All rights reserved