Arylthiols as highly chemoselective and environmentally benign radical reducing agents

The Journal of Organic Chemistry
Shigeru Yamago, Atsushi Matsumoto

Abstract

Arylthiols serve as excellent environmentally benign reducing agents for organotellurium, organostibine, and organobismuthine compounds under radical conditions. Both small molecules and macromolecules possessing these heteroatom groups are reduced under moderate thermal conditions to give near quantitative yields in most cases. The reduction shows high chemoselectivity with respect to the heteroatom compounds; the reactivity decreases in the order alkylbismuthines, alkylstibines, and alkyltellurides, while simple alkyl iodides could not be reduced. Alkyltellurides are selectively reduced in the presence of alkyl iodides even when an excess amount of arylthiol is used. Furthermore, alkylstibines are also selectively reduced in the presence of alkyltellurides. Moreover, the reduction conditions are compatible with the presence of a variety of polar functional groups in the substrates, products, and solvents, which are not tolerant under ionic and metal-catalyzed conditions. Carbon-carbon bond formation is possible with use of the carbon-centered radicals that are generated. The results clearly reveal the synthetic utility of arylthiols in organic synthesis.

References

Feb 19, 2002·Chemical Reviews·Chryssostomos ChatgilialogluIlhyong Ryu
Oct 24, 2002·Chemistry : a European Journal·Jonathan M WhiteRobert W Gable
Jul 17, 2003·Journal of the American Chemical Society·Atsushi GotoJun-Ichi Yoshida
Jul 17, 2004·The Journal of Organic Chemistry·Cecilia Ericsson, Lars Engman
Oct 28, 2004·Journal of the American Chemical Society·Shigeru YamagoTakeshi Fukuda
Sep 21, 2005·Chemical Society Reviews·Dominique LecaMax Malacria
Oct 13, 2005·Journal of the American Chemical Society·Davide PozziPhilippe Renaud
Jan 25, 2007·Journal of the American Chemical Society·Deborah M SmithJack R Norton
Jul 2, 2001·Angewandte Chemie·Sunggak KimJoo-Yong Yoon

❮ Previous
Next ❯

Citations

Feb 10, 2009·Journal of the American Chemical Society·Shigeru YamagoYasuyuki Nakamura
Feb 22, 2018·Chemical Communications : Chem Comm·Yulong KuangTianning Diao
Oct 8, 2019·Journal of the American Chemical Society·Qiao Lin, Tianning Diao

❮ 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.