Pd(II)-catalysed meta-C-H functionalizations of benzoic acid derivatives

Nature Communications
Shangda LiGang Li

Abstract

Benzoic acids are highly important structural motifs in drug molecules and natural products. Selective C-H bond functionalization of benzoic acids will provide synthetically useful tools for step-economical organic synthesis. Although direct ortho-C-H functionalizations of benzoic acids or their derivatives have been intensely studied, the ability to activate meta-C-H bond of benzoic acids or their derivatives in a general manner via transition-metal catalysis has been largely unsuccessful. Although chelation-assisted meta-C-H functionalization of electron-rich arenes was reported, chelation-assisted meta-C-H activation of electron-poor arenes such as benzoic acid derivatives remains a formidable challenge. Herein, we report a general protocol for meta-C-H olefination of benzoic acid derivatives using a nitrile-based sulfonamide template. A broad range of benzoic acid derivatives are meta-selectively olefinated using molecular oxygen as the terminal oxidant. The meta-C-H acetoxylation, product of which is further transformed at the meta-position, is also reported.

References

Aug 22, 2001·Accounts of Chemical Research·C JiaY Fujiwara
Feb 26, 2004·Journal of the American Chemical Society·Allison R DickMelanie S Sanford
Mar 6, 2007·Journal of the American Chemical Society·Ramesh GiriJin-Quan Yu
Jul 26, 2007·Journal of the American Chemical Society·Hendrich A ChiongOlafs Daugulis
Sep 12, 2007·Journal of the American Chemical Society·Kami L Hull, Melanie S Sanford
Mar 20, 2009·Journal of the American Chemical Society·Yang-Hui ZhangJin-Quan Yu
Mar 21, 2009·Science·Robert J Phipps, Matthew J Gaunt
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Aug 27, 2010·Chemistry : a European Journal·Tetsuya Satoh, Masahiro Miura
Oct 23, 2010·Angewandte Chemie·Hung A DuongMatthew J Gaunt
Mar 9, 2011·Journal of the American Chemical Society·Thomas W LyonsMelanie S Sanford
Mar 11, 2011·Organic Letters·Lutz AckermannRubén Vicente
Mar 12, 2011·Chemical Reviews·Jean Le Bras, Jacques Muzart
Apr 16, 2011·Journal of the American Chemical Society·Mengchun YeJin-Quan Yu
Sep 29, 2011·Angewandte Chemie·Marion H EmmertMelanie S Sanford
Nov 4, 2011·Journal of the American Chemical Society·Ourida SaidiChristopher G Frost
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Jan 31, 2012·Angewandte Chemie·Joanna Wencel-DelordFrank Glorius
Jun 29, 2012·Nature·Dasheng LeowJin-Quan Yu
Sep 29, 2012·Science·Liam T BallChristopher A Russell
Mar 29, 2013·Journal of the American Chemical Society·Nora Hofmann, Lutz Ackermann
Apr 26, 2013·Journal of the American Chemical Society·Hui-Xiong DaiJin-Quan Yu
May 18, 2013·Journal of the American Chemical Society·Ruja ShresthaJohn F Hartwig
Sep 4, 2013·Journal of the American Chemical Society·Gregory B BoursalianTobias Ritter
Nov 19, 2013·Journal of the American Chemical Society·Li WanJin-Quan Yu
Dec 12, 2013·Journal of the American Chemical Society·Sunggi LeeKian L Tan
Mar 14, 2014·Nature·Ri-Yuan TangJin-Quan Yu
Jul 10, 2014·Journal of the American Chemical Society·Guoqiang YangJin-Quan Yu
Dec 6, 2014·Chemical Communications : Chem Comm·Jingchang ZhangQifeng Wang
Dec 20, 2014·Organic & Biomolecular Chemistry·Jiong Yang

❮ Previous
Next ❯

Citations

May 18, 2016·Journal of the American Chemical Society·Zhoulong FanAo Zhang
Oct 8, 2016·Journal of the American Chemical Society·Peng WangJin-Quan Yu
Nov 18, 2016·Chemical Communications : Chem Comm·Soham MaityDebabrata Maiti
Apr 11, 2017·Angewandte Chemie·Milan BeraDebabrata Maiti
Apr 27, 2017·The Journal of Organic Chemistry·Hao XieFengzhi Zhang
May 10, 2017·Organic Letters·Long YangGang Li
Feb 2, 2017·Chemical Communications : Chem Comm·Peng-Xiang LingBing-Feng Shi
Feb 17, 2017·Angewandte Chemie·Sukdev BagDebabrata Maiti
Apr 28, 2016·Organic & Biomolecular Chemistry·Aniruddha DeyDebabrata Maiti
Jul 6, 2017·Organic & Biomolecular Chemistry·Andrew J PatersonChristopher G Frost
Jul 20, 2017·Organic Letters·Bo LiBing-Feng Shi
Nov 16, 2016·Chemical Communications : Chem Comm·Atanu ModakDebabrata Maiti
Apr 28, 2018·Angewandte Chemie·Ramasamy JayarajanDebabrata Maiti
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Jan 10, 2018·Angewandte Chemie·Hao ChenManuel van Gemmeren
Mar 15, 2019·Chemical Communications : Chem Comm·Huaxin ZhaoWen Wan
Nov 30, 2018·Angewandte Chemie·Aniruddha DeyDebabrata Maiti
May 11, 2019·Angewandte Chemie·Parthasarathy GandeepanLutz Ackermann
Oct 1, 2019·Chemical Communications : Chem Comm·Shuguang XieZhong Jin
Mar 21, 2020·Chemistry : a European Journal·Sandeep PimparkarDebabrata Maiti
Aug 6, 2020·Angewandte Chemie·Debabrata MaitiAdithyaraj Koodan
Jul 5, 2017·Chemistry : a European Journal·Qiankun Li, Eric M Ferreira
May 26, 2017·Chemical Society Reviews·Lucy PingSang-Gi Lee
Sep 7, 2019·Chemical Science·Uttam DuttaDebabrata Maiti
Oct 4, 2017·Chemical Science·Wengang Xu, Naohiko Yoshikai
Aug 10, 2020·Chemistry : a European Journal·Isaac ChoiLutz Ackermann
May 15, 2021·Science·Uttam DuttaDebabrata Maiti
Jun 25, 2021·Chemical Science·Wajid AliDebabrata Maiti
Jun 25, 2021·Chemical Science·Trisha BhattacharyaDebabrata Maiti
Mar 3, 2020·Chemical Science·Alexander F WilliamsChristopher J Cordier
May 22, 2020·Journal of the American Chemical Society·Guangrong MengJin-Quan Yu

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR

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.