Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.

The Journal of Organic Chemistry
Joseph R MartinelliStephen L Buchwald

Abstract

A method for the Pd-catalyzed carbonylation of aryl bromides has been developed using Xantphos as the ligand. This method is effective for the direct synthesis of Weinreb amides, primary and secondary benzamides, and methyl esters from the corresponding aryl bromides at atmospheric pressure. In addition, a putative catalytic intermediate, (Xanphos)Pd(Br)benzoyl, was prepared and an X-ray crystal structure was obtained revealing an unusual cis-coordination mode of Xantphos in this palladium-acyl complex.

References

Apr 13, 2000·Angewandte Chemie·M Beller, M Eckert
Dec 26, 2001·Chemical Reviews·P W van LeeuwenP Dierkes
May 23, 2002·Journal of the American Chemical Society·Jingjun Yin, Stephen L Buchwald
Apr 26, 2003·The Journal of Organic Chemistry·Obaidur RahmanBengt Långström
Aug 15, 2003·Organic Letters·Mohamed S Mohammed Ahmed, Atsunori Mori
Nov 25, 2003·The Journal of Organic Chemistry·Dmitry V Kadnikov, Richard C Larock
Jun 18, 2004·Organic Letters·Jennifer Albaneze-WalkerJerry A Murry
Sep 17, 2004·Angewandte Chemie·Tsumoru Morimoto, Kiyomi Kakiuchi
Jul 30, 2005·The Journal of Organic Chemistry·Giorgio AbbiatiElisabetta Rossi
Sep 24, 2005·Organic Letters·Mohamed S Mohamed AhmedAtsunori Mori
Nov 24, 2005·Angewandte Chemie·Stefan KlausMatthias Beller
Sep 28, 2006·Journal of the American Chemical Society·Vladimir V Grushin, William J Marshall
Oct 20, 2006·Organic Letters·Chaoxian CaiYongkui Sun
Jan 29, 2008·The Journal of Organic Chemistry·A DeagostinoPaolo Venturello
Feb 9, 2008·Journal of the American Chemical Society·Rachel H MundayStephen L Buchwald

❮ Previous
Next ❯

Citations

Aug 22, 2012·Journal of the American Chemical Society·Igor PochorovskiFrancois Diederich
May 31, 2011·The Journal of Organic Chemistry·Dinesh N SawantBhalchandra M Bhanage
Jan 17, 2012·The Journal of Organic Chemistry·Stephanie HoArturo Orellana
Mar 31, 2012·The Journal of Organic Chemistry·Klaus BjerglundTroels Skrydstrup
Jul 28, 2011·Organic Letters·Dennis U NielsenTroels Skrydstrup
Feb 28, 2013·Organic Letters·Stig D FriisTroels Skrydstrup
Apr 6, 2013·Organic Letters·Stephen G DaviesJames E Thomson
Aug 16, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Yinghuai ZhuAbdul M Seayad
Sep 29, 2012·Science·Liam T BallChristopher A Russell
May 27, 2014·Nuclear Medicine and Biology·Patrik NordemanGunnar Antoni
Oct 6, 2016·Organic Letters·Stephen J Dwight, Sergiy Levin
Mar 10, 2017·Angewandte Chemie·Kishore NatteRajenahally V Jagadeesh
Jul 23, 2016·Angewandte Chemie·Hai-Yang ZhaoXingang Zhang
Dec 3, 2016·Organic & Biomolecular Chemistry·Seger Van MileghemWim M De Borggraeve
Jan 31, 2015·Chemical Communications : Chem Comm·Zhong LianTroels Skrydstrup
Apr 10, 2015·Chemical Communications : Chem Comm·Zhong LianTroels Skrydstrup
Sep 15, 2015·Organic & Biomolecular Chemistry·Yong ZhengLi-Jiang Xuan
May 4, 2017·Chemistry : a European Journal·Raffaella BucciMaria Luisa Gelmi
Oct 11, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sara RoslinJonas Eriksson
Dec 20, 2014·Chemical Communications : Chem Comm·Zhong LianTroels Skrydstrup
Dec 20, 2014·Chemical Communications : Chem Comm·Hideyuki KonishiKei Manabe
Nov 16, 2016·Chemical Communications : Chem Comm·Kelly F FirthDouglas W Stephan
Mar 11, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Rostam Ali MollaSk Manirul Islam
Aug 14, 2012·Chemistry : a European Journal·Beneesh P BabuJan-E Bäckvall
Jan 6, 2011·Chemistry : a European Journal·Xiao-Feng WuMatthias Beller
Nov 23, 2013·Chemistry : a European Journal·Dennis U NielsenTroels Skrydstrup
Sep 10, 2014·Chemistry : a European Journal·Suman De Sarkar, Lutz Ackermann
Sep 10, 2014·Chemistry, an Asian Journal·Longfei RanZheng-Hui Guan
Aug 15, 2018·Chemistry : a European Journal·Karoline T NeumannTroels Skrydstrup
Nov 7, 2013·Organic & Biomolecular Chemistry·Chenxu HuZhengkai Li
Nov 19, 2013·Chemical Communications : Chem Comm·Huizhen LiuPaul J Dyson

❮ 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.