Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups

Journal of the American Chemical Society
Gang LiJin-Quan Yu

Abstract

Ortho-C(sp(2))-H olefination and acetoxylation of broadly useful synthetic building blocks phenylacetyl Weinreb amides, esters, and ketones are developed without installing an additional directing group. The interplay between the distal weak coordination and the ligand-acceleration is crucial for these reactions to proceed under mild conditions. The tolerance of longer distance between the target C-H bonds and the directing functional groups also allows for the functionalizations of more distal C-H bonds in hydrocinnamoyl ketones, Weinreb amides, and biphenyl Weinreb amides. Mechanistically, the coordination of these carbonyl groups and the bisdentate amino acid ligand with Pd(II) centers provides further evidence for our early hypothesis that the carbonyl groups of the potassium carboxylate are responsible for the directed C-H activation of carboxylic acids.

References

Aug 22, 2001·Accounts of Chemical Research·C JiaY Fujiwara
Feb 20, 2002·Chemical Reviews·Alexander E. Shilov, Georgiy B. Shul'pin
Feb 21, 2002·Journal of the American Chemical Society·Maarten D K BoelePiet W N M van Leeuwen
Feb 26, 2004·Journal of the American Chemical Society·Allison R DickMelanie S Sanford
Jan 11, 2007·Chemical Reviews·Dino AlbericoMark Lautens
Mar 6, 2007·Journal of the American Chemical Society·Ramesh GiriJin-Quan Yu
Jun 20, 2007·Chemical Society Reviews·Ilya V Seregin, Vladimir Gevorgyan
Jul 26, 2007·Journal of the American Chemical Society·Hendrich A ChiongOlafs Daugulis
May 16, 2008·Journal of the American Chemical Society·Dong-Hui WangJin-Quan Yu
Oct 7, 2008·Journal of the American Chemical Society·Masayuki Wasa, Jin-Quan Yu
Oct 7, 2008·Journal of the American Chemical Society·Ramesh Giri, Jin-Quan Yu
Dec 11, 2008·Journal of the American Chemical Society·Dong-Hui WangJin-Quan Yu
May 14, 2009·Journal of the American Chemical Society·Xisheng WangJin-Quan Yu
Jun 26, 2009·Accounts of Chemical Research·Olafs DaugulisDmitry Shabashov
Jul 8, 2009·Journal of the American Chemical Society·Masayuki WasaJin-Quan Yu
Oct 1, 2009·Journal of the American Chemical Society·Yang-Hui Zhang, Jin-Quan Yu
Dec 17, 2009·The Journal of Organic Chemistry·Guan-Wu Wang, Ting-Ting Yuan
Dec 19, 2009·Journal of the American Chemical Society·Bing-Feng ShiJin-Quan Yu
Dec 22, 2009·Journal of the American Chemical Society·Bin XiaoLei Liu
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
Mar 2, 2010·Journal of the American Chemical Society·Masayuki WasaJin-Quan Yu
Apr 3, 2010·Journal of the American Chemical Society·Yi LuJin-Quan Yu
May 4, 2010·Journal of the American Chemical Society·Nicolas GuimondKeith Fagnou
Sep 22, 2010·Journal of the American Chemical Society·Keary M EngleJin-Quan Yu
Jan 12, 2011·Journal of the American Chemical Society·Bin XiaoLei Liu
Jan 27, 2011·Angewandte Chemie·Frederic W PatureauFrank Glorius
Feb 1, 2011·Journal of the American Chemical Society·Souvik RakshitFrank Glorius
Feb 8, 2011·Chemical Society Reviews·Will R Gutekunst, Phil S Baran
Mar 3, 2011·Angewandte Chemie·Géraldine Rousseau, Bernhard Breit
Mar 11, 2011·Chemical Society Reviews·Lindsay McMurrayMatthew J Gaunt
Mar 12, 2011·Chemical Reviews·Jean Le Bras, Jacques Muzart
Apr 2, 2011·Journal of the American Chemical Society·Nicolas GuimondKeith Fagnou

❮ Previous
Next ❯

Citations

Feb 26, 2016·Organic Letters·Aitziber IrastorzaArkaitz Correa
Dec 23, 2016·Journal of the American Chemical Society·Xi-Hai LiuJin-Quan Yu
Mar 30, 2017·The Journal of Organic Chemistry·Kenji MatsumotoMitsuru Shindo
Apr 11, 2017·Angewandte Chemie·Ming ShangJin-Quan Yu
Jul 18, 2017·Journal of the American Chemical Society·Thomas J CoxonMichael C Willis
Apr 8, 2017·Organic & Biomolecular Chemistry·Xinyu ZhangQiufeng Huang
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Sep 18, 2015·Chemistry : a European Journal·Youla SuHequan Yao
Jan 10, 2018·Angewandte Chemie·Hao ChenManuel van Gemmeren
Oct 3, 2018·Chemical Communications : Chem Comm·Renjie ChenSunliang Cui
Jan 10, 2020·Chemical Communications : Chem Comm·Shang-Zheng SunHui-Xiong Dai
Sep 23, 2020·Organic & Biomolecular Chemistry·Hirotsugu SuzukiTakanori Matsuda
May 10, 2020·Angewandte Chemie·Han Seul ParkJin-Quan Yu
Apr 10, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Xian-Ying ShiChao-Jun Li
Oct 29, 2017·Nature Communications·Bingwei ZhouCongyang Wang
Mar 1, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jagadeesh Kalepu, Lukasz T Pilarski
Dec 20, 2018·Chemical Communications : Chem Comm·Yang-Jie MaoDan-Qian Xu
Apr 3, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wengang WuRongxin Yuan
Jul 1, 2020·Chemistry : a European Journal·Qingqing BuLutz Ackermann
Mar 3, 2021·Angewandte Chemie·Xuefeng TanLutz Ackermann
May 27, 2021·The Journal of Organic Chemistry·Muniyappa Vijaykumar, Benudhar Punji
Jun 25, 2021·Chemical Science·Trisha BhattacharyaDebabrata Maiti
Mar 3, 2020·Chemical Science·Alexander F WilliamsChristopher J Cordier
Jul 20, 2021·Journal of the American Chemical Society·Alexander UttryManuel van Gemmeren
Apr 11, 2018·Organic Letters·Xing-Qian NingDan-Qian Xu

❮ 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.