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Cross-coupling and dehalogenation reactions catalyzed by (N-heterocyclic carbene)Pd(allyl)Cl complexes.
J Org Chem. 2004 Apr 30; 69(9):3173-80.JO

Abstract

A series of well-defined, air- and moisture-stable (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes has been used in several catalytic reactions: Suzuki-Miyaura cross-coupling, catalytic dehalogenation of aryl halides, and aryl amination. The scope of the three processes using various substrates was examined. A general system involving the use of (IPr)Pd(allyl)Cl as catalyst and NaO(t)Bu as base has proven to be highly active for the Suzuki-Miyaura cross-coupling of activated and unactivated aryl chlorides and bromides, for the catalytic dehalogenation of aryl chlorides, and for the catalytic aryl amination of aryl triflates. All reactions proceed in short reaction times and at mild temperatures. The system has also proven to be compatible with the microwave-assisted Suzuki-Miyaura cross-coupling and catalytic dehalogenation processes, affording yields similar to those of the conventionally heated analogous reactions.

Authors+Show Affiliations

Department of Chemistry, University of New Orleans, New Orleans, Louisiana 70148, USA.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15104459

Citation

Navarro, Oscar, et al. "Cross-coupling and Dehalogenation Reactions Catalyzed By (N-heterocyclic carbene)Pd(allyl)Cl Complexes." The Journal of Organic Chemistry, vol. 69, no. 9, 2004, pp. 3173-80.
Navarro O, Kaur H, Mahjoor P, et al. Cross-coupling and dehalogenation reactions catalyzed by (N-heterocyclic carbene)Pd(allyl)Cl complexes. J Org Chem. 2004;69(9):3173-80.
Navarro, O., Kaur, H., Mahjoor, P., & Nolan, S. P. (2004). Cross-coupling and dehalogenation reactions catalyzed by (N-heterocyclic carbene)Pd(allyl)Cl complexes. The Journal of Organic Chemistry, 69(9), 3173-80.
Navarro O, et al. Cross-coupling and Dehalogenation Reactions Catalyzed By (N-heterocyclic carbene)Pd(allyl)Cl Complexes. J Org Chem. 2004 Apr 30;69(9):3173-80. PubMed PMID: 15104459.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cross-coupling and dehalogenation reactions catalyzed by (N-heterocyclic carbene)Pd(allyl)Cl complexes. AU - Navarro,Oscar, AU - Kaur,Harneet, AU - Mahjoor,Parisa, AU - Nolan,Steven P, PY - 2004/4/24/pubmed PY - 2004/4/24/medline PY - 2004/4/24/entrez SP - 3173 EP - 80 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 9 N2 - A series of well-defined, air- and moisture-stable (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes has been used in several catalytic reactions: Suzuki-Miyaura cross-coupling, catalytic dehalogenation of aryl halides, and aryl amination. The scope of the three processes using various substrates was examined. A general system involving the use of (IPr)Pd(allyl)Cl as catalyst and NaO(t)Bu as base has proven to be highly active for the Suzuki-Miyaura cross-coupling of activated and unactivated aryl chlorides and bromides, for the catalytic dehalogenation of aryl chlorides, and for the catalytic aryl amination of aryl triflates. All reactions proceed in short reaction times and at mild temperatures. The system has also proven to be compatible with the microwave-assisted Suzuki-Miyaura cross-coupling and catalytic dehalogenation processes, affording yields similar to those of the conventionally heated analogous reactions. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15104459/Cross_coupling_and_dehalogenation_reactions_catalyzed_by__N_heterocyclic_carbene_Pd_allyl_Cl_complexes_ DB - PRIME DP - Unbound Medicine ER -
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