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Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions.
J Am Chem Soc. 2006 Mar 29; 128(12):4101-11.JA

Abstract

A series of (NHC)Pd(R-allyl)Cl complexes [NHC: IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene; R = H, Me, gem-Me2, Ph] have been synthesized and fully characterized. When compared to (NHC)Pd(allyl)Cl, substitution at the terminal position of the allyl scaffold favors a more facile activation step. This translates into higher catalytic activity in the Suzuki-Miyaura and Buchwald-Hartwig reactions, allowing for the coupling of unactivated aryl chlorides at room temperature in minutes. In the Suzuki-Miyaura reaction, aryl triflates, bromides, and chlorides react with boronic acids using very low catalyst loading. In the N-aryl amination reaction, a wide range of substrates has been coupled efficiently; primary-, secondary-, alkyl-, or aryl-amines react in high yields with unactivated, neutral, and activated aryl chlorides and bromides. In both reactions, extremely hindered substrates such as tri-ortho-substituted biaryls and tetra-ortho-substituted diarylamines can be produced without loss of activity. Finally, the present catalytic system has proven to be efficient with as low as 10 parts-per-million (ppm) of precatalyst in the Buchwald-Hartwig reaction and 50 ppm in the Suzuki-Miyaura reaction.

Authors+Show Affiliations

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

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16551119

Citation

Marion, Nicolas, et al. "Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic Carbene) Complexes for Room-temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions." Journal of the American Chemical Society, vol. 128, no. 12, 2006, pp. 4101-11.
Marion N, Navarro O, Mei J, et al. Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions. J Am Chem Soc. 2006;128(12):4101-11.
Marion, N., Navarro, O., Mei, J., Stevens, E. D., Scott, N. M., & Nolan, S. P. (2006). Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions. Journal of the American Chemical Society, 128(12), 4101-11.
Marion N, et al. Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic Carbene) Complexes for Room-temperature Suzuki-Miyaura and Buchwald-Hartwig Reactions. J Am Chem Soc. 2006 Mar 29;128(12):4101-11. PubMed PMID: 16551119.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Modified (NHC)Pd(allyl)Cl (NHC = N-heterocyclic carbene) complexes for room-temperature Suzuki-Miyaura and Buchwald-Hartwig reactions. AU - Marion,Nicolas, AU - Navarro,Oscar, AU - Mei,Jianguo, AU - Stevens,Edwin D, AU - Scott,Natalie M, AU - Nolan,Steven P, PY - 2006/3/23/pubmed PY - 2006/3/23/medline PY - 2006/3/23/entrez SP - 4101 EP - 11 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 12 N2 - A series of (NHC)Pd(R-allyl)Cl complexes [NHC: IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N'-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene; R = H, Me, gem-Me2, Ph] have been synthesized and fully characterized. When compared to (NHC)Pd(allyl)Cl, substitution at the terminal position of the allyl scaffold favors a more facile activation step. This translates into higher catalytic activity in the Suzuki-Miyaura and Buchwald-Hartwig reactions, allowing for the coupling of unactivated aryl chlorides at room temperature in minutes. In the Suzuki-Miyaura reaction, aryl triflates, bromides, and chlorides react with boronic acids using very low catalyst loading. In the N-aryl amination reaction, a wide range of substrates has been coupled efficiently; primary-, secondary-, alkyl-, or aryl-amines react in high yields with unactivated, neutral, and activated aryl chlorides and bromides. In both reactions, extremely hindered substrates such as tri-ortho-substituted biaryls and tetra-ortho-substituted diarylamines can be produced without loss of activity. Finally, the present catalytic system has proven to be efficient with as low as 10 parts-per-million (ppm) of precatalyst in the Buchwald-Hartwig reaction and 50 ppm in the Suzuki-Miyaura reaction. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/16551119/Modified__NHC_Pd_allyl_Cl__NHC_=_N_heterocyclic_carbene__complexes_for_room_temperature_Suzuki_Miyaura_and_Buchwald_Hartwig_reactions_ DB - PRIME DP - Unbound Medicine ER -
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