Iridium-Catalyzed Formyl-Selective Deuteration of Aldehydes

Angewandte Chemie
William J KerrTell Tuttle

Abstract

We report the first direct catalytic method for formyl-selective deuterium labeling of aromatic aldehydes under mild conditions, using an iridium-based catalyst designed to favor formyl over aromatic C-H activation. A good range of aromatic aldehydes is selectively labeled, and a one-pot labeling/olefination method is also described. Computational studies support kinetic product control over competing aromatic labeling and decarbonylation pathways.

References

Dec 17, 2005·Organic & Biomolecular Chemistry·Phillip J BlackJonathan M J Williams
Sep 25, 2007·Angewandte Chemie·Jens AtzrodtJochen Zimmermann
Feb 29, 2008·Journal of the American Chemical Society·Peter FristrupRobert Madsen
Jan 14, 2010·Chemical Reviews·David BalcellsOdile Eisenstein
Nov 11, 2010·Journal of the American Chemical Society·Jesús CamposErnesto Carmona
Jun 15, 2011·Chemical Society Reviews·Joanna Wencel-DelordFrank Glorius
Apr 10, 2012·Accounts of Chemical Research·Brian G HashiguchiRoy A Periana
Jun 19, 2012·Journal of the American Chemical Society·Lorenz NeubertMatthias Beller
Sep 22, 2012·Angewandte Chemie·Nadine KuhlFrank Glorius
Oct 31, 2012·Chemistry : a European Journal·Esben P K Olsen, Robert Madsen
Jan 18, 2013·Chemistry : a European Journal·Joel F HooperMichael C Willis
Nov 29, 2013·Journal of Labelled Compounds & Radiopharmaceuticals·Alison R CochraneGöran N Nilsson
Jul 22, 2014·Chemistry : a European Journal·Michael ParmentierDieter Muri
Sep 11, 2014·Organic & Biomolecular Chemistry·Alan R KennedyMarc Reid
Jun 30, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jennifer DevlinTell Tuttle

❮ Previous
Next ❯

Citations

Mar 21, 2018·Chemical Society Reviews·Manuel Iglesias, Luis A Oro
Oct 13, 2017·Angewandte Chemie·Jens AtzrodtMarc Reid
Apr 1, 2018·Journal of Labelled Compounds & Radiopharmaceuticals·Richard P Nugent, Crist N Filer
Oct 24, 2018·Angewandte Chemie·Muliang ZhangJin Xie
Nov 13, 2019·Journal of Labelled Compounds & Radiopharmaceuticals·William J KerrLaura C Paterson
Aug 25, 2020·Organic & Biomolecular Chemistry·Guang-Qi HuWei Huang
Feb 16, 2021·Organic Letters·Guang-Qi HuHong-Hai Zhang
Jan 1, 2019·Nature Catalysis·Huihui GengWei Wang
May 18, 2021·Chemistry : a European Journal·Ramón AzpírozJesús J Pérez-Torrente
Mar 21, 2019·The Journal of Organic Chemistry·Kolluru SrinivasChepuri V Ramana
Jan 23, 2020·Chemical Reviews·Qun ZhaoMichal Szostak
Mar 9, 2018·Organic Letters·Xiangmin LiChunquan Sheng
Feb 25, 2021·ACS Catalysis·Yueteng ZhangWei Wang

❮ 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.