Mechanochemical Iridium(III)-Catalyzed C-H Bond Amidation of Benzamides with Sulfonyl Azides under Solvent-Free Conditions in a Ball Mill

Angewandte Chemie
Gary N HermannCarsten Bolm

Abstract

Mechanochemical conditions have been applied to an iridium(III)-catalyzed C-H bond amidation process for the first time. In the absence of solvent, the mechanochemical activation enables the formation of an iridium species that catalyzes the ortho-selective amidation of benzamides with sulfonyl azides as the nitrogen source. As the reaction proceeds in the absence of organic solvents without external heating and yields the desired products in excellent yields within short reaction times, this method constitutes a powerful, fast, and environmentally benign alternative to the common solvent-based standard approaches.

References

May 20, 2006·Nature Chemical Biology·Ryan Hili, Andrei K Yudin
May 21, 2010·Beilstein Journal of Organic Chemistry·Franziska BernhardtBernd Ondruschka
Mar 10, 2011·Chemical Society Reviews·Achim StolleBernd Ondruschka
Mar 15, 2011·Chemical Communications : Chem Comm·Rico ThorwirthUlrich S Schubert
May 25, 2011·Journal of the American Chemical Society·Emmanuel Ferrer FlegeauAnny Jutand
Sep 6, 2011·Chemical Society Reviews·Stuart L JamesDaniel C Waddell
May 26, 2012·Journal of the American Chemical Society·Ji Young KimSukbok Chang
Oct 30, 2012·Chemical Communications : Chem Comm·Valérie DeclerckFrédéric Lamaty
Apr 26, 2013·Chemistry : a European Journal·Jiyu KimSukbok Chang
May 1, 2013·Chemical Communications : Chem Comm·M BhanuchandraAkhila K Sahoo
May 11, 2013·Chemical Society Reviews·Guan-Wu Wang
May 17, 2013·Chemical Communications : Chem Comm·Qing-Zhong ZhengNing Jiao
Jun 19, 2013·Organic Letters·Vedhagiri S ThirunavukkarasuLutz Ackermann
Jun 22, 2013·Angewandte Chemie·Kwangmin ShinSukbok Chang
Aug 21, 2013·Journal of the American Chemical Society·Jaeyune RyuSukbok Chang
Oct 1, 2013·Chemical Society Reviews·Jitender Bariwal, Erik Van der Eycken
Oct 2, 2013·The Journal of Organic Chemistry·Donggun LeeSukbok Chang
Nov 12, 2013·Chemical Communications : Chem Comm·Vedhagiri S ThirunavukkarasuLutz Ackermann
Nov 22, 2013·Chemical Communications : Chem Comm·Davin TanTomislav Friščić
Jan 1, 2014·Journal of the American Chemical Society·Hyun Jin KimSukbok Chang
Jan 24, 2014·Journal of the American Chemical Society·Sae Hume ParkSukbok Chang
Mar 13, 2014·Chemistry : a European Journal·Changduo PanChengjian Zhu
Mar 19, 2014·The Journal of Organic Chemistry·Hao WangBin Xu
Aug 26, 2014·Chemistry : a European Journal·Donghyeon GwonSukbok Chang
Aug 29, 2014·Chemical Communications : Chem Comm·Taek KangSukbok Chang
Sep 16, 2014·The Journal of Organic Chemistry·Kwangmin Shin, Sukbok Chang
Feb 11, 2015·Journal of the American Chemical Society·Jean-Louis DoTomislav Friščić
Feb 18, 2015·Chemistry : a European Journal·Donggun Lee, Sukbok Chang
Jul 15, 2015·Chemical Communications : Chem Comm·José G Hernández, Carsten Bolm

❮ Previous
Next ❯

Citations

Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Jan 13, 2017·The Journal of Organic Chemistry·José G Hernández, Carsten Bolm
Apr 25, 2017·Chemical Communications : Chem Comm·Veeranjaneyulu Lanke, Kandikere Ramaiah Prabhu
May 14, 2017·Angewandte Chemie·Huai-Wei WangJin-Quan Yu
Jun 3, 2016·Chemistry : a European Journal·Ying ChengCarsten Bolm
May 16, 2017·Chemistry : a European Journal·Ying SimFelipe García
Jul 26, 2017·The Journal of Organic Chemistry·Haichao MaWei Yu
May 31, 2017·Chemistry : a European Journal·Yeongyu HwangSukbok Chang
Oct 28, 2016·Chemical Communications : Chem Comm·Andrea MonasManda Ćurić
Jul 12, 2018·Chemical Communications : Chem Comm·Christian SchumacherJosé G Hernández
Jun 20, 2018·Chemistry : a European Journal·Alen BjelopetrovićManda Ćurić
Oct 24, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Thomas E ShawTitel Jurca
Feb 15, 2019·Chemistry : a European Journal·Yadong PangHajime Ito
Oct 25, 2017·Beilstein Journal of Organic Chemistry·Tapas Kumar AcharPrasenjit Mal
Jul 12, 2019·Angewandte Chemie·Tomislav FriščićHatem M Titi
May 22, 2018·Chemical Science·Joseph L HowardDuncan L Browne
Oct 27, 2016·Chemistry : a European Journal·Yun-Fei ZhangZhang-Jie Shi
Aug 25, 2017·Chemistry : a European Journal·José G Hernández
Oct 4, 2017·Chemical Science·Joel M Andersen, James Mack
May 17, 2017·Chemical Science·Qingquan LuFrank Glorius
Oct 9, 2020·Angewandte Chemie·Shengjun NiLukasz T Pilarski
Jun 3, 2021·Pharmaceutics·Mizraín Solares-BrionesJuan M Germán-Acacio
May 24, 2019·The Journal of Organic Chemistry·Manoj KumarAkhilesh K Verma
Sep 14, 2017·The Journal of Organic Chemistry·Xinpeng JiangChuanming Yu
Jan 5, 2019·Journal of the American Chemical Society·Stipe LukinIvan Halasz

❮ 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.