Rhodium-Catalyzed Annelation of Benzoic Acids with α,β-Unsaturated Ketones with Cleavage of C-H, CO-OH, and C-C Bonds

Angewandte Chemie
Guodong ZhangLukas J Gooßen

Abstract

In the presence of a [Cp*RhCl2 ]2 catalyst, the Lewis acid In(OTf)3 , and the mild base Na2 CO3 , aromatic carboxylates and α,β-unsaturated ketones undergo a unique hydroarylation/Claisen/retro-Claisen process to give the corresponding indanones. In this carboxylate-directed ortho-C-H annelation, the C-COR bond of the ketone and the CO-OH group of the aromatic carboxylate are cleaved, and the hydroxy group is transferred from the aromatic to the aliphatic acyl residue. This reactivity is synthetically useful, particularly when starting from cyclic ketones, which are converted into indanones bearing aliphatic carboxylate side chains, thus greatly increasing the molecular complexity of aromatic carboxylates in a single step.

References

Aug 22, 2001·Accounts of Chemical Research·C JiaY Fujiwara
Feb 20, 2002·Chemical Reviews·Alexander E. Shilov, Georgiy B. Shul'pin
Nov 17, 2005·Journal of the American Chemical Society·Kousik KunduAndrew T Morehead
Aug 5, 2006·Science·Lukas J GoossenLaura M Levy
Jun 20, 2007·Chemical Society Reviews·Ilya V Seregin, Vladimir Gevorgyan
Jul 26, 2007·Journal of the American Chemical Society·Hendrich A ChiongOlafs Daugulis
Sep 6, 2007·Angewandte Chemie·Atsushi KawataKazuhiko Takai
May 15, 2009·Chemical Reviews·Denise A ColbyJonathan A Ellman
Nov 6, 2010·Chemical Reviews·Chang-Liang SunZhang-Jie Shi
Aug 19, 2011·Organic & Biomolecular Chemistry·Luo YangChao-Jun Li
Jun 15, 2012·Journal of the American Chemical Society·Feng YinChaozhong Li
Sep 1, 2012·Chemical Reviews·Percia Beatrice ArockiamPierre H Dixneuf
Oct 11, 2013·Chemistry : a European Journal·Stéphanie Dupuy, Steven P Nolan
Oct 16, 2013·Journal of the American Chemical Society·Peter S Thuy-BounJin-Quan Yu
Nov 18, 2014·Journal of the American Chemical Society·Junfeng Yang, Naohiko Yoshikai
Jul 18, 2015·Chemical Society Reviews·Zhongxing HuangGuangbin Dong
Aug 15, 2015·Journal of the American Chemical Society·Guolin ChengJin-Quan Yu
Oct 13, 2016·Chemistry : a European Journal·Martin Pichette Drapeau, Lukas J Gooßen
Oct 22, 2016·Angewandte Chemie·Agostino BiaforaLukas J Gooßen
Oct 22, 2016·Chemical Reviews·Jay A Labinger
Jan 14, 2017·Chemical Reviews·Yudong YangJingsong You
Mar 8, 2017·Chemical Reviews·Ye WeiWeiping Su
Apr 6, 2017·Chemical Reviews·Rui ShangEiichi Nakamura
May 12, 2017·Chemical Communications : Chem Comm·Marc FontIgor Larrosa
May 26, 2017·Chemical Communications : Chem Comm·Kiran R BettadapurKandikere Ramaiah Prabhu
Jul 2, 2017·European Journal of Medicinal Chemistry·Siddappa A PatilShivaputra A Patil
Jul 13, 2017·Chemical Reviews·Robert H Crabtree, Aiwen Lei

❮ Previous
Next ❯

Citations

Dec 17, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hamid Azizollahi, José-Antonio García-López

❮ 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.