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Bis(1-adamantyl)(2-morpholinophenyl)phosphine (Mor-DalPhos)

Lundgren, Rylan J. (2014) Bis(1-adamantyl)(2-morpholinophenyl)phosphine (Mor-DalPhos). In: e-EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons , Hoboken, N.J.. ISBN 9780470842898. https://resolver.caltech.edu/CaltechAUTHORS:20160404-092037342

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Abstract

(ligand employed in transition metal-catalyzed reactions) Alternate Name: di(1-adamantyl)-2-morpholinophenylphosphine. Physical Data: mp 219–224 °C. Solubility: soluble in most polar organic solvents. Form Supplied in: White to pale yellow powder or crystals. Also commercially available as preformed Au-ligand complexes such as (MeCN)(Mor-Dalphos)Au(I) SbF_6 and [Mor-Dalphos]Au(I)Cl. Analysis of Reagent Purity: NMR, Elemental Analysis. Preparative Method: Pd-catalyzed cross-coupling of N-(2-bromophenyl)morpholine and diadamantyl phosphine. Handling, Storage, and Precautions: the phosphine is not particularly sensitive to air or moisture although precautions, such as storage under inert atmosphere in a cool place, should be taken during long-term storage. Bis(1-adamantyl)(2-morpholinophenyl)phosphine (Mor-DalPhos) is a phosphine ligand that has been employed in Pd-catalyzed cross-coupling reactions and Au-catalyzed hydroamination and [3+2] annulations. This ligand, when combined with an appropriate Pd-source, is particularly effective for promoting selective monoarylation processes between aryl electrophiles and nucleophiles such as ammonia, hydrazine, and acetone.


Item Type:Book Section
Related URLs:
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http://dx.doi.org/10.1002/047084289X.rn01672DOIEncyclopedia entry
http://onlinelibrary.wiley.com/doi/10.1002/047084289X.rn01672/abstractPublisherEncyclopedia entry
Additional Information:© 2001 John Wiley & Sons, Ltd. Published Online: 27 May 2014. Article includes InChi structural models.
Record Number:CaltechAUTHORS:20160404-092037342
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160404-092037342
Official Citation:Lundgren, R. J. 2014. Bis(1-adamantyl)(2-morpholinophenyl)phosphine (Mor-DalPhos). e-EROS Encyclopedia of Reagents for Organic Synthesis. 1–2
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:65885
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:18 Apr 2016 21:04
Last Modified:03 Oct 2019 09:51

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