Rhodium-catalysed direct hydroarylation of alkenes and alkynes with phosphines through phosphorous-assisted C-H activation

Nature Communications
Dingyi WangZhuangzhi Shi

Abstract

Biarylphosphines have been widely applied as ligands in various synthetic methods, especially in transition-metal-catalysed carbon-carbon and carbon-heteroatom bond cross-coupling reactions. Based on the outstanding properties of the parent scaffolds, a general method for in situ modification of the commercial tertiary phosphine ligands to access a series of ligands is in high demand. Here we show that a rhodium-catalysed system is introduced for the hydroarylation of alkenes and alkynes with tertiary phosphines through P(III)-chelation assisted C-H activation. A series of ligand libraries containing alkyl and alkenyl substituted groups with different steric and electronic properties are obtained in high yields. Furthermore, several experimental studies are performed to uncover the key mechanistic features of the linear-selective hydroarylation of alkenes and branch-selective hydroarylation of alkynes.

References

Apr 6, 2006·Angewandte Chemie·Ryo ShintaniTamio Hayashi
Dec 18, 2007·Angewandte Chemie·Jeffrey B Johnson, Tomislav Rovis
Oct 29, 2008·Organic Letters·Kai ChengYuhong Zhang
Jan 3, 2003·Angewandte Chemie·Robin B BedfordMichael E Limmert
Jan 19, 2010·Chemical Reviews·Thomas W Lyons, Melanie S Sanford
May 6, 2010·Journal of the American Chemical Society·Derek J SchipperKeith Fagnou
Aug 18, 2010·Journal of the American Chemical Society·Ke GaoNaohiko Yoshikai
Dec 17, 2010·Journal of the American Chemical Society·Ke Gao, Naohiko Yoshikai
Feb 12, 2011·Journal of the American Chemical Society·Zhijian LiuJohn F Hartwig
Jun 28, 2011·Journal of the American Chemical Society·Michael FindlaterMaurice Brookhart
Oct 1, 2011·Journal of the American Chemical Society·Pin-Sheng LeeNaohiko Yoshikai
Dec 14, 2011·Accounts of Chemical Research·Denise A ColbyJonathan A Ellman
Dec 15, 2011·Accounts of Chemical Research·Keary M EngleJin-Quan Yu
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Sep 28, 2012·Journal of the American Chemical Society·Jaesung KwakSukbok Chang
Dec 12, 2012·Angewandte Chemie·Pin-Sheng Lee, Naohiko Yoshikai
Jan 5, 2013·Journal of the American Chemical Society·Bingwei ZhouCongyang Wang
Oct 9, 2013·Organic Letters·Hong-Li WangShang-Dong Yang
Dec 18, 2013·Chemical Society Reviews·Yoshihiko Yamamoto
Mar 1, 2014·Accounts of Chemical Research·Ke Gao, Naohiko Yoshikai
Jul 2, 2014·Chemical Society Reviews·Fengzhi Zhang, David R Spring
Jul 16, 2014·Journal of the American Chemical Society·Giacomo E M CrisenzaJohn F Bower
May 1, 2015·Journal of the American Chemical Society·Yusuke Ebe, Takahiro Nishimura
Jul 18, 2015·Chemical Society Reviews·Zhongxing HuangGuangbin Dong
Apr 14, 2016·Chemical Society Reviews·T GenschJ Wencel-Delord
Apr 26, 2016·Chemical Reviews·Vadim P BoyarskiyAleksander V Vasilyev
Sep 16, 2016·Angewandte Chemie·Wengang Xu, Naohiko Yoshikai
Jan 27, 2017·Chemical Reviews·Zhe DongGuangbin Dong
May 10, 2017·Accounts of Chemical Research·Yan-Na MaShang-Dong Yang
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu
Sep 19, 2017·Journal of the American Chemical Society·Dong Xing, Guangbin Dong
May 5, 2018·Journal of the American Chemical Society·Arun Jyoti Borah, Zhuangzhi Shi
Jul 20, 2018·Journal of the American Chemical Society·Simon GrélaudJohn F Bower
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Nov 28, 2018·Chemical Reviews·Parthasarathy GandeepanLutz Ackermann

❮ Previous
Next ❯

Citations

Feb 26, 2021·Organic Letters·Hui-Bei XuLin Dong
Jan 26, 2021·Angewandte Chemie·Toryn DaltonFrank Glorius
Mar 13, 2021·Accounts of Chemical Research·Jian Wen, Zhuangzhi Shi
Apr 7, 2021·The Journal of Organic Chemistry·Dhananjay YadavMaya Shankar Singh
Jun 30, 2021·Chemical Communications : Chem Comm·En-Kai XiaoPeng Chen

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray
column chromatography

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.