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A Fast Track to Indoles and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides.
Org Lett. 2019 12 20; 21(24):10143-10148.OL

Abstract

A complementary site selective ortho- vs ipso-amination of aryl halides using non-electrophilic amine sources for construction of indole scaffolds is reported. A palladium-catalyzed alkyne insertion/C-H activation/palladacycle amination via merger of three easily diversified components including iodoarenes, alkynes, and amines delivers indoles with different substitution patterns even in gram scales. By employing ortho-bromoanilines, a consecutive annulative π-extension of indoles proceeds to construct indolo[1,2-f]phenanthridine scaffolds via four C-C and C-N bond formations in one pot.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Jafarpour F
School of Chemistry, College of Science , University of Tehran , 14155-6455 Tehran , Iran.
Ghasemi M
Faculty of Chemistry , Kharazmi University , No. 43. Mofateh Street, Enghelab Ave. , 15719-14911 Tehran , Iran.
Mohaghegh F
School of Chemistry, College of Science , University of Tehran , 14155-6455 Tehran , Iran.
Asgari S
School of Chemistry, College of Science , University of Tehran , 14155-6455 Tehran , Iran.
Habibi A
Faculty of Chemistry , Kharazmi University , No. 43. Mofateh Street, Enghelab Ave. , 15719-14911 Tehran , Iran.

Pub Type(s)

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

Language

eng

PubMed ID

31793789

Citation

Jafarpour, Farnaz, et al. "A Fast Track to Indoles and Annulated Indoles Through Ortho- Vs ipso-Amination of Aryl Halides." Organic Letters, vol. 21, no. 24, 2019, pp. 10143-10148.
Jafarpour F, Ghasemi M, Mohaghegh F, et al. A Fast Track to Indoles and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides. Org Lett. 2019;21(24):10143-10148.
Jafarpour, F., Ghasemi, M., Mohaghegh, F., Asgari, S., & Habibi, A. (2019). A Fast Track to Indoles and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides. Organic Letters, 21(24), 10143-10148. https://doi.org/10.1021/acs.orglett.9b04202
Jafarpour F, et al. A Fast Track to Indoles and Annulated Indoles Through Ortho- Vs ipso-Amination of Aryl Halides. Org Lett. 2019 12 20;21(24):10143-10148. PubMed PMID: 31793789.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A Fast Track to Indoles and Annulated Indoles through ortho- vs ipso-Amination of Aryl Halides. AU - Jafarpour,Farnaz, AU - Ghasemi,Mehran, AU - Mohaghegh,Farid, AU - Asgari,Sara, AU - Habibi,Azizollah, Y1 - 2019/12/03/ PY - 2019/12/4/pubmed PY - 2019/12/4/medline PY - 2019/12/4/entrez SP - 10143 EP - 10148 JF - Organic letters JO - Org Lett VL - 21 IS - 24 N2 - A complementary site selective ortho- vs ipso-amination of aryl halides using non-electrophilic amine sources for construction of indole scaffolds is reported. A palladium-catalyzed alkyne insertion/C-H activation/palladacycle amination via merger of three easily diversified components including iodoarenes, alkynes, and amines delivers indoles with different substitution patterns even in gram scales. By employing ortho-bromoanilines, a consecutive annulative π-extension of indoles proceeds to construct indolo[1,2-f]phenanthridine scaffolds via four C-C and C-N bond formations in one pot. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31793789/A_Fast_Track_to_Indoles_and_Annulated_Indoles_through_ortho__vs_ipso_Amination_of_Aryl_Halides_ DB - PRIME DP - Unbound Medicine ER -