Photosensitized oxidative addition to gold(I) enables alkynylative cyclization of o-alkylnylphenols with iodoalkynes

Nature Chemistry
Zhonghua XiaLouis Fensterbank

Abstract

The well-established oxidative addition-reductive elimination pathway is the most followed one in transition metal-catalysed cross-coupling reactions. While readily occurring with a series of transition metals, gold(I) complexes have shown some reluctance to undergo oxidative addition unless special sets of ligands on gold(I), reagents or reaction conditions are used. Here we show that under visible-light irradiation, an iridium photocatalyst triggers-via triplet sensitization-the oxidative addition of an alkynyl iodide onto a vinylgold(I) intermediate to deliver C(sp)2-C(sp) coupling products after reductive elimination. Mechanistic and modelling studies support that an energy-transfer event takes place, rather than a redox pathway. This particular mode of activation in gold homogenous catalysis was applied in several dual catalytic processes. Alkynylbenzofuran derivatives were obtained from o-alkynylphenols and iodoalkynes in the presence of catalytic gold(I) and iridium(III) complexes under blue light-emitting diode irradiation.

References

Jan 22, 2010·Journal of the American Chemical Society·Teresa de Haro, Cristina Nevado
Oct 13, 2010·Organic Letters·Matthew N HopkinsonVéronique Gouverneur
Jan 21, 2012·Chemical Society Reviews·Le-Ping Liu, Gerald B Hammond
Mar 2, 2012·Journal of the American Chemical Society·Weibo WangBo Xu
Sep 12, 2012·Angewandte Chemie·Zhan Lu, Tehshik P Yoon
Apr 10, 2013·Journal of the American Chemical Society·Basudev SahooFrank Glorius
May 15, 2013·Angewandte Chemie·Yifan LiJérôme Waser
Feb 26, 2014·Accounts of Chemical Research·Louis Fensterbank, Max Malacria
Apr 16, 2014·Journal of the American Chemical Society·Xing-zhong ShuF Dean Toste
May 20, 2014·Journal of the American Chemical Society·Matthew S WinstonF Dean Toste
Aug 30, 2014·Organic Letters·Oliver DumeleFrançois Diederich
Oct 1, 2014·Journal of the American Chemical Society·Maximilian JoostDidier Bourissou
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren
May 8, 2015·Journal of the American Chemical Society·Seung Jun HwangDaniel G Nocera
Jan 16, 2016·Angewandte Chemie·Maximilian JoostDidier Bourissou
Jan 20, 2016·Chemical Society Reviews·Zhitong ZhengLiming Zhang
Feb 19, 2016·Chemistry : a European Journal·Frank GloriusAleyda Garza-Sanchez
Mar 10, 2016·Journal of the American Chemical Society·Patricia García-Domínguez, Cristina Nevado
Apr 21, 2016·Chemical Communications : Chem Comm·Long HuangA Stephen K Hashmi
Apr 26, 2016·Chemical Reviews·Kazimer L SkubiTehshik P Yoon
May 18, 2016·Chemical Communications : Chem Comm·Eric Omar Asomoza-SolísSusana Porcel
Jul 28, 2016·Chemical Communications : Chem Comm·Vincent Gauchot, Ai-Lan Lee
Oct 19, 2016·Accounts of Chemical Research·Matthew N HopkinsonFrank Glorius
Sep 23, 2016·Journal of the American Chemical Society·Drew R HeitzGary A Molander
Sep 23, 2016·Journal of the American Chemical Society·Benjamin J Shields, Abigail G Doyle
Sep 20, 2017·Nature Communications·Abdallah ZeineddineDidier Bourissou
Mar 20, 2018·Journal of the American Chemical Society·Matthew J HarperChristopher A Russell
May 19, 2018·Angewandte Chemie·Quan-Quan ZhouWen-Jing Xiao
Jan 1, 2016·Chemical Science·Suhong KimF Dean Toste
Jan 1, 2016·Chemical Science·Adrian Tlahuext-AcaFrank Glorius
Aug 8, 2018·Nature Chemistry·Michael TedersFrank Glorius
Aug 9, 2018·Chemical Society Reviews·Felix Strieth-KalthoffFrank Glorius
Dec 29, 2018·Beilstein Journal of Organic Chemistry·Atsushi KagaShunsuke Chiba

❮ Previous
Next ❯

Citations

Sep 26, 2019·Angewandte Chemie·Svenja TaschinskiJohannes E M N Klein
Jan 18, 2020·Angewandte Chemie·Jamie A CadgeChristopher A Russell
Mar 24, 2020·Angewandte Chemie·Chetan C ChintawarNitin T Patil
May 22, 2020·Angewandte Chemie·Mathilde RigouletDidier Bourissou
Aug 7, 2019·Nature Chemistry·Euan B McLean, Ai-Lan Lee
Jan 19, 2020·Angewandte Chemie·Hai-Jun TangChao Feng
Jun 2, 2020·Chemistry : a European Journal·Susana Porcel, Ignacio Medina-Mercado
Jan 26, 2021·Chemical Reviews·Sina WitzelJin Xie
Apr 4, 2020·Organic Letters·Joan G MayansAntonio M Echavarren
Dec 17, 2019·Organic Letters·Peizhong XieTeck-Peng Loh
Aug 20, 2020·Journal of the American Chemical Society·Pedro D García-FernándezJosé M Lassaletta
Nov 19, 2021·Chemical Reviews·Amy Y ChanDavid W C MacMillan
Dec 8, 2021·Organic & Biomolecular Chemistry·Ali Osman Karatavuk

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray
NMR

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.