Regiocontrolled direct C4 and C2-methyl thiolation of indoles under rhodium-catalyzed mild conditions

Chemical Communications : Chem Comm
Saurabh MaityRajarshi Samanta

Abstract

A straightforward Rh(iii)-catalyzed general strategy was developed for the site-selective remote C4 (sp2) and C2 (sp3)-methyl thiolation of an indole core, keeping the oxime directing group at the C3 position. The transformation was accomplished under mild conditions with a wide scope and functional group tolerance. The directing group can easily be removed after operation. Methyl substitution at the C2 position of the indole core led to C2 (sp3)-methyl thiolation.

References

Jul 18, 2002·Antimicrobial Agents and Chemotherapy·Takashi AsaiL David Sibley
Mar 6, 2003·Bioorganic & Medicinal Chemistry Letters·Angela CasiniClaudiu T Supuran
Oct 23, 2004·The Journal of Organic Chemistry·Yasunari MaedaSakae Uemura
Nov 29, 2005·Natural Product Reports·Tomomi Kawasaki, Kazuhiro Higuchi
Feb 14, 2006·Organic Letters·Matthew TudgeGuy R Humphrey
Dec 7, 2006·Journal of the American Chemical Society·Sulagna PaulMilton R Smith
Apr 13, 2007·Chemical Reviews·Amanda R Murphy, Jean M J Fréchet
Oct 20, 2007·Chemical Reviews·Mohamed MellahEmmanuelle Schulz
Mar 5, 2010·Journal of the American Chemical Society·Daniel W RobbinsJohn F Hartwig
Apr 13, 2010·Chemical Reviews·Anna J Kochanowska-Karamyan, Mark T Hamann
Oct 1, 2011·The Journal of Organic Chemistry·Sadananda RanjitXiaogang Liu
Oct 30, 2012·Journal of the American Chemical Society·Ly Dieu TranOlafs Daugulis
Dec 5, 2012·Beilstein Journal of Organic Chemistry·Gianluigi BrogginiSilvia Gazzola
May 25, 2013·The Journal of Organic Chemistry·Jingjing LiangYanxing Jia
Nov 30, 2013·Chemistry : a European Journal·Yaxi YangYuanchao Li
Jan 15, 2014·The Journal of Organic Chemistry·Hua LiuShu-Li You
Jan 30, 2014·Journal of Medicinal Chemistry·Richard D TaylorAlastair D G Lawson
Jul 10, 2014·Journal of the American Chemical Society·Guoqiang YangJin-Quan Yu
Oct 14, 2014·Chemical Society Reviews·Chao ShenXiaogang Liu
Oct 25, 2014·The Journal of Organic Chemistry·Richard P LoachMohammad Movassaghi
Dec 2, 2014·The Journal of Organic Chemistry·Renhua QiuNobuaki Kambe
Dec 3, 2014·European Journal of Medicinal Chemistry·Ming-Zhi ZhangGuang-Fu Yang
Mar 19, 2015·Angewandte Chemie·Suhelen Vásquez-CéspedesFrank Glorius
Mar 21, 2015·The Journal of Organic Chemistry·Heng-Ying XiongXavier Pannecoucke
Mar 31, 2015·Chemical Communications : Chem Comm·Sheng-Yi YanBing-Feng Shi
Mar 31, 2015·Organic Letters·Xie WangShuang-Feng Yin
Apr 10, 2015·Chemical Communications : Chem Comm·Xiaohan YeXiaodong Shi
Aug 11, 2015·Journal of the American Chemical Society·Yu FengPhil S Baran
Oct 30, 2015·Angewandte Chemie·Lanting XuDawei Ma
Dec 22, 2015·The Journal of Organic Chemistry·Wucheng XieBaiquan Wang
Dec 29, 2015·Journal of the American Chemical Society·Youqing YangZhuangzhi Shi
Jan 9, 2016·The Journal of Organic Chemistry·Debapratim DasRajarshi Samanta
May 14, 2016·Organic & Biomolecular Chemistry·Zengqiang Song, Andrey P Antonchick
Jul 1, 2016·Journal of the American Chemical Society·Youqing YangZhuangzhi Shi
Jul 21, 2016·Angewandte Chemie·Tobias GenschFrank Glorius
Aug 9, 2016·Chemistry : a European Journal·Thomas Müller, Lutz Ackermann
Nov 5, 2016·The Journal of Organic Chemistry·Lanting XuDawei Ma
Sep 15, 2016·The Journal of Organic Chemistry·Feng GaoHong Liu

❮ Previous
Next ❯

Citations

Sep 20, 2018·Chemical Communications : Chem Comm·Mahadev Sharanappa SherikarKandikere Ramaiah Prabhu
Jun 25, 2019·Chemical Communications : Chem Comm·Jitan ZhangMeihua Xie
Oct 2, 2020·Organic & Biomolecular Chemistry·Shi-Biao TangYa-Fei Ji
Aug 14, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Mieko Arisawa, Masahiko Yamaguchi
May 28, 2019·Chemical Communications : Chem Comm·Bidhan Ghosh, Rajarshi Samanta
Apr 30, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Satabdi BeraRajarshi Samanta
Oct 1, 2019·The Journal of Organic Chemistry·Mohit KumarDipankar Koley
Aug 25, 2018·Organic Letters·Saurabh MaityRajarshi Samanta
Feb 6, 2019·The Journal of Organic Chemistry·Ujjwal Karmakar, Rajarshi Samanta
Mar 21, 2020·The Journal of Organic Chemistry·Mahadev Sharanappa SherikarKandikere Ramaiah Prabhu
Aug 3, 2018·Organic Letters·Chandrababu Naidu KonaMasahiro Miura
Aug 14, 2020·The Journal of Organic Chemistry·Wei-Hong SongGuoyong Song
Sep 24, 2021·Chemical Communications : Chem Comm·Jayanta GhoraiPazhamalai Anbarasan

❮ 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.