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Palladium-catalyzed one-pot three- or four-component coupling of aryl iodides, alkynes, and amines through C-N bond cleavage: efficient synthesis of indole derivatives.
Chemistry. 2014 Feb 24; 20(9):2605-12.C

Abstract

An efficient synthesis of N-substituted indole derivatives was realized by combining the Pd-catalyzed one-pot multicomponent coupling approach with cleavage of the C(sp(3))-N bonds. Three or four components of aryl iodides, alkynes, and amines were involved in this coupling process. The cyclopentadiene-phosphine ligand showed high efficiency. A variety of aryl iodides, including cyclic and acyclic tertiary amino aryl iodides, and substituted 1-bromo-2-iodobenzene derivatives could be used. Both symmetric and unsymmetric alkynes substituted with alkyl, aryl, or trimethylsilyl groups could be applied. Cyclic secondary amines such as piperidine, morpholine, 4-methylpiperidine, 1-methylpiperazine, 2-methylpiperidine, and acyclic amines including secondary and primary amines all showed good reactivity. Further application of the resulting indole derivatives was demonstrated by the synthesis of benzosilolo[2,3-b]indole.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hao W
Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China), Fax: (+86) 10-62751708.
Geng W
No affiliation info available
Zhang WX
No affiliation info available
Xi Z
No affiliation info available

MeSH

AlkynesAminesCatalysisHeterocyclic CompoundsIndolesIodidesLigandsMolecular StructurePalladiumPhosphines

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24449487

Citation

Hao, Wei, et al. "Palladium-catalyzed One-pot Three- or Four-component Coupling of Aryl Iodides, Alkynes, and Amines Through C-N Bond Cleavage: Efficient Synthesis of Indole Derivatives." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 9, 2014, pp. 2605-12.
Hao W, Geng W, Zhang WX, et al. Palladium-catalyzed one-pot three- or four-component coupling of aryl iodides, alkynes, and amines through C-N bond cleavage: efficient synthesis of indole derivatives. Chemistry. 2014;20(9):2605-12.
Hao, W., Geng, W., Zhang, W. X., & Xi, Z. (2014). Palladium-catalyzed one-pot three- or four-component coupling of aryl iodides, alkynes, and amines through C-N bond cleavage: efficient synthesis of indole derivatives. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(9), 2605-12. https://doi.org/10.1002/chem.201304215
Hao W, et al. Palladium-catalyzed One-pot Three- or Four-component Coupling of Aryl Iodides, Alkynes, and Amines Through C-N Bond Cleavage: Efficient Synthesis of Indole Derivatives. Chemistry. 2014 Feb 24;20(9):2605-12. PubMed PMID: 24449487.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed one-pot three- or four-component coupling of aryl iodides, alkynes, and amines through C-N bond cleavage: efficient synthesis of indole derivatives. AU - Hao,Wei, AU - Geng,Weizhi, AU - Zhang,Wen-Xiong, AU - Xi,Zhenfeng, Y1 - 2014/01/21/ PY - 2013/10/29/received PY - 2014/1/23/entrez PY - 2014/1/23/pubmed PY - 2014/12/15/medline KW - cleavage reactions KW - indoles KW - multicomponent reactions KW - palladium KW - synthetic methods SP - 2605 EP - 12 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 9 N2 - An efficient synthesis of N-substituted indole derivatives was realized by combining the Pd-catalyzed one-pot multicomponent coupling approach with cleavage of the C(sp(3))-N bonds. Three or four components of aryl iodides, alkynes, and amines were involved in this coupling process. The cyclopentadiene-phosphine ligand showed high efficiency. A variety of aryl iodides, including cyclic and acyclic tertiary amino aryl iodides, and substituted 1-bromo-2-iodobenzene derivatives could be used. Both symmetric and unsymmetric alkynes substituted with alkyl, aryl, or trimethylsilyl groups could be applied. Cyclic secondary amines such as piperidine, morpholine, 4-methylpiperidine, 1-methylpiperazine, 2-methylpiperidine, and acyclic amines including secondary and primary amines all showed good reactivity. Further application of the resulting indole derivatives was demonstrated by the synthesis of benzosilolo[2,3-b]indole. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24449487/Palladium_catalyzed_one_pot_three__or_four_component_coupling_of_aryl_iodides_alkynes_and_amines_through_C_N_bond_cleavage:_efficient_synthesis_of_indole_derivatives_ DB - PRIME DP - Unbound Medicine ER -