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The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)₃ and PCy₃ as Ligands

Fu, Gregory C. (2008) The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)₃ and PCy₃ as Ligands. Accounts of Chemical Research, 41 (11). pp. 1555-1564. ISSN 0001-4842. PMCID PMC2645957. doi:10.1021/ar800148f. https://resolver.caltech.edu/CaltechAUTHORS:20200626-123754582

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Abstract

Metal-catalyzed coupling reactions of aryl electrophiles with organometallics and with olefins serve as unusually effective tools for forming new carbon−carbon bonds. By 1998, researchers had developed catalysts that achieved reactions of aryl iodides, bromides, and triflates. Nevertheless, many noteworthy challenges remained; among them were couplings of aryl iodides, bromides, and triflates under mild conditions (at room temperature, for example), couplings of hindered reaction partners, and couplings of inexpensive aryl chlorides. This Account highlights some of the progress that has been made in our laboratory over the past decade, largely through the appropriate choice of ligand, in achieving these synthetic objectives. In particular, we have established that palladium in combination with a bulky trialkylphosphine accomplishes a broad spectrum of coupling processes, including Suzuki, Stille, Negishi, and Heck reactions. These methods have been applied in a wide array of settings, such as natural-product synthesis, materials science, and bioorganic chemistry.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/ar800148fDOIArticle
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2645957/PubMed CentralArticle
ORCID:
AuthorORCID
Fu, Gregory C.0000-0002-0927-680X
Alternate Title:The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands
Additional Information:© 2008 American Chemical Society. Received 24 June 2008. Published online 24 October 2008. Published in issue 18 November 2008. This article is part of the Cross Coupling special issue. I am extremely grateful to the co-workers who contributed to this program, particularly Adam F. Littke, who initiated our studies. Primary support for this investigation has been provided by the National Institutes of Health (National Institute of General Medical Sciences, Grant R01-GM62871), with supplementary funding furnished by Merck Research Laboratories and by Novartis. I thank Prof. Amir Hoveyda (Boston College) and Prof. Alan Sellinger (Institute of Materials Research & Engineering) for assistance with two of the illustrations.
Funders:
Funding AgencyGrant Number
NIHR01-GM62871
Merck Research LaboratoriesUNSPECIFIED
NovartisUNSPECIFIED
Issue or Number:11
PubMed Central ID:PMC2645957
DOI:10.1021/ar800148f
Record Number:CaltechAUTHORS:20200626-123754582
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20200626-123754582
Official Citation:The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands Gregory C. Fu Accounts of Chemical Research 2008 41 (11), 1555-1564 DOI: 10.1021/ar800148f
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:104086
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:26 Jun 2020 21:22
Last Modified:16 Nov 2021 18:28

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