N-Heterocyclic Carbene-Catalyzed Decarboxylative Alkylation of Aldehydes

Journal of the American Chemical Society
Takuya IshiiHirohisa Ohmiya

Abstract

We found that N-heterocyclic carbene catalysis promoted the unprecedented decarboxylative coupling of aryl aldehydes and tertiary or secondary alkyl carboxylic acid-derived redox-active esters to produce aryl alkyl ketones. The mild and transition-metal-free reaction conditions are attractive features of this method. The power of this protocol was demonstrated by the functionalization of pharmaceutical drugs and natural product. A reaction pathway involving single electron transfer from an enolate form of Breslow intermediate to a redox ester followed by recombination of the resultant radical pair to form a carbon-carbon bond is proposed.

References

Feb 22, 2002·The Journal of Organic Chemistry·Toshiki NishinoNoboru Sonoda
Mar 2, 2002·The Journal of Organic Chemistry·Yi-Chun HuangChien-Hong Cheng
Jun 12, 2003·Chemical Reviews·Stephen W Ragsdale
Nov 26, 2004·Journal of the American Chemical Society·Mathieu PucheaultJean-Pierre Genet
Apr 13, 2006·Journal of the American Chemical Society·Anita E MattsonKarl A Scheidt
May 22, 2008·Chemical Reviews·Ronald Kluger, Kai Tittmann
Jul 19, 2008·Journal of the American Chemical Society·Jiwu RuanJianliang Xiao
Oct 11, 2008·Angewandte Chemie·Joyram GuinArmido Studer
Jun 27, 2014·Nature·Matthew N HopkinsonFrank Glorius
Feb 5, 2015·Journal of the American Chemical Society·Yuexia ZhangYonggui Robin Chi
May 21, 2015·Chemical Reviews·Darrin M FlaniganTomislav Rovis
Aug 11, 2015·Journal of the American Chemical Society·Nicholas A White, Tomislav Rovis
Jul 6, 2016·The Journal of Organic Chemistry·Basuli Suchand, Gedu Satyanarayana
May 18, 2017·Journal of the American Chemical Society·Lisa CandishFrank Glorius
Aug 7, 2017·Journal of the American Chemical Society·Xiaheng Zhang, David W C MacMillan
Sep 21, 2017·Angewandte Chemie·Satobhisha MukherjeeFrank Glorius
Oct 1, 2015·Chemical Science·Julia RehbeinJenny Phan
Dec 19, 2018·Journal of the American Chemical Society·Vianney RegnierDavid Martin

❮ Previous
Next ❯

Citations

Sep 7, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mario PrejanòTiziana Marino
May 23, 2019·Angewandte Chemie·Dirk Leifert, Armido Studer
Dec 10, 2019·Angewandte Chemie·Andreas MavroskoufisMatthew N Hopkinson
Mar 5, 2020·Chemical Communications : Chem Comm·Hai-Bin YangChuande Wu
Nov 14, 2019·Topics in Current Chemistry·Kazunori Nagao, Hirohisa Ohmiya
Jun 3, 2020·Proceedings of the National Academy of Sciences of the United States of America·Alison A BaylyKarl A Scheidt
May 28, 2019·Angewandte Chemie·Runjiang Song, Yonggui Robin Chi
Nov 27, 2020·Chemical Communications : Chem Comm·Shilpa Barik, Akkattu T Biju
Oct 10, 2020·Chemistry : a European Journal·Qing-Zhu LiJun-Long Li
Dec 2, 2020·Chemistry : a European Journal·Yuya NakatsujiYoshiji Takemoto
Jan 13, 2021·Organic Letters·Hai-Bin Yang, Dan-Hong Wan
Mar 25, 2021·Journal of the American Chemical Society·Kun Liu, Armido Studer
Apr 8, 2021·Nature Communications·Qing-Yuan MengArmido Studer
May 6, 2021·Organic & Biomolecular Chemistry·Yasushi YoshidaMasami Sakamoto
May 12, 2021·Chemical Society Reviews·Áron PéterDavid J Procter
Jun 8, 2021·Chemical Science·Takuya IshiiHirohisa Ohmiya
Jun 8, 2021·Chemical Science·Jing LiuWen-Jing Xiao
Jun 24, 2021·Nature Communications·Yuki MatsukiHirohisa Ohmiya
Jul 16, 2021·Tetrahedron·Joshua L Zhu, Karl A Scheidt
Jun 8, 2021·Angewandte Chemie·Anna V BayKarl A Scheidt
Apr 4, 2019·Journal of the American Chemical Society·Shengyang NiPhil S Baran
Jan 7, 2020·Organic Letters·Bei ZhangJian Wang
Jan 4, 2020·Journal of the American Chemical Society·Shotaro ShibutaniHirohisa Ohmiya
Aug 27, 2019·Journal of the American Chemical Society·Takuya IshiiHirohisa Ohmiya
Oct 9, 2021·The Journal of Organic Chemistry·Fengjuan ChenWei Zeng
Nov 18, 2021·Organic Letters·Yuxing CaiYong Huang

❮ 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.