Highly Regio- and Stereoselective Hydrosilylation of Internal Thioalkynes under Mild Conditions

Angewandte Chemie
Shengtao DingJianwei Sun

Abstract

A general and mild hydrosilylation of thioalkynes is described. With the cationic catalyst [Cp*Ru(MeCN)3 ](+) and the bulky silane (TMSO)3 SiH, a range of thioalkynes underwent smooth hydrosilylation at room temperature with excellent α regioselectivity and syn stereoselectivity. DFT calculations provided important insight into the mechanism, particularly the unusual syn selectivity with the [Cp*Ru(MeCN)3 ](+) catalyst. The sulfenyl group in the substrates was found to provide important chelation stabilization to direct the reaction through a new mechanistic pathway.

References

Jan 1, 1996·Cytogenetics and Cell Genetics·L WalterG Levan
Dec 14, 2001·Journal of the American Chemical Society·B M Trost, Z T Ball
Jul 4, 2002·Journal of the American Chemical Society·Barry M TrostThomas Jöge
Jan 8, 2003·Journal of the American Chemical Society·Barry M Trost, Zachary T Ball
Jul 31, 2003·Angewandte Chemie·Barry M TrostThomas Jöge
May 20, 2004·Angewandte Chemie·Henri Brunner
Oct 28, 2004·Journal of the American Chemical Society·Barry M Trost, Zachary T Ball
Jun 17, 2005·Angewandte Chemie·René HermatschweilerMaria José Calhorda
Dec 15, 2005·Journal of the American Chemical Society·Barry M Trost, Zachary T Ball
Jun 22, 2006·Medicinal Research Reviews·D Christopher Meadows, Jacquelyn Gervay-Hague
Jun 21, 2007·Chemical Communications : Chem Comm·Takanori MatsudaMasahiro Murakami
May 15, 2008·The Journal of Organic Chemistry·Guillaume Berthon-GellozIstván E Markó
Jul 23, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Tell TuttleJohann Weis
Aug 10, 2010·Journal of the American Chemical Society·Douglas A Rooke, Eric M Ferreira
Sep 20, 2011·Journal of the American Chemical Society·Marie-Gabrielle BraunSamir Z Zard
Jun 21, 2012·Organic Letters·Douglas A Rooke, Eric M Ferreira
Sep 12, 2012·Angewandte Chemie·Karin RadkowskiAlois Fürstner
Mar 9, 2013·Organic Letters·Hui Zhou, Christina Moberg
Mar 12, 2013·Journal of the American Chemical Society·Wanxiang ZhaoJianwei Sun
Nov 1, 2013·Angewandte Chemie·Basker Sundararaju, Alois Fürstner
Dec 3, 2013·Journal of the American Chemical Society·María J BernalEduardo Sola
Feb 28, 2014·Angewandte Chemie·Stephan M Rummelt, Alois Fürstner
Jan 9, 2015·Journal of the American Chemical Society·Gui-Juan ChengYun-Dong Wu

❮ Previous
Next ❯

Citations

Jun 15, 2017·Chemistry : a European Journal·Xiaohan YeXiaodong Shi
May 24, 2018·Chemical Communications : Chem Comm·Xin-Qi ZhuLong-Wu Ye
Aug 26, 2017·Angewandte Chemie·Raju Jannapu ReddyPaul W Davies
Oct 13, 2018·Chemical Communications : Chem Comm·Guojiao WuAxel Jacobi von Wangelin
Jan 22, 2020·Chemical Communications : Chem Comm·Weiwei GaoShengtao Ding
Sep 5, 2020·Chemistry : a European Journal·Éric GodinShawn K Collins
Mar 18, 2021·The Journal of Organic Chemistry·Mathieu MorencyShawn K Collins
Oct 10, 2019·Journal of the American Chemical Society·Lijuan SongJianwei Sun
Jul 16, 2020·Journal of the American Chemical Society·Qiang FengJianwei Sun
Jul 16, 2020·Organic Letters·Éric GodinShawn K Collins
Sep 23, 2021·The Journal of Organic Chemistry·Wenli HuMingzhong Cai

❮ 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.