Site-selective C–H nitration of N-aryl-7-azaindoles under palladium(II) catalysis

Rina Chun; Saegun Kim; Sang Hoon Han; Ashok Kumar Pandey; Neeraj Kumar Mishra; In Su Kim

doi:10.1016/j.tetlet.2018.09.025

Site-selective C–H nitration of N-aryl-7-azaindoles under palladium(II) catalysis

Rina Chun
, Saegun Kim
, Sang Hoon Han
, Ashok Kumar Pandey
, Neeraj Kumar Mishra
, In Su Kim

Department of Pharmacy

Sungkyunkwan University

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

The site-selective C–H nitration reaction of 7-azaindoles with t-butyl nitrite under palladium catalysis is described. This protocol provides an efficient method for the construction of ortho-nitrated N-aryl-7-azaindoles with excellent site-selectivity and functional group compatibility. The formed 7-azaindole derivatives can be readily transformed into 7-azaindoles containing an aniline functional group under palladium-catalyzed hydrogenation conditions.

Original language	English
Pages (from-to)	3848-3852
Number of pages	5
Journal	Tetrahedron Letters
Volume	59
Issue number	43
DOIs	https://doi.org/10.1016/j.tetlet.2018.09.025
State	Published - 24 Oct 2018

Keywords

Azaindoles
C–H functionalization
Nitration
Palladium
Regioselectivity

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10.1016/j.tetlet.2018.09.025

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title = "Site-selective C–H nitration of N-aryl-7-azaindoles under palladium(II) catalysis",

abstract = "The site-selective C–H nitration reaction of 7-azaindoles with t-butyl nitrite under palladium catalysis is described. This protocol provides an efficient method for the construction of ortho-nitrated N-aryl-7-azaindoles with excellent site-selectivity and functional group compatibility. The formed 7-azaindole derivatives can be readily transformed into 7-azaindoles containing an aniline functional group under palladium-catalyzed hydrogenation conditions.",

keywords = "Azaindoles, C–H functionalization, Nitration, Palladium, Regioselectivity",

author = "Rina Chun and Saegun Kim and Han, \{Sang Hoon\} and Pandey, \{Ashok Kumar\} and Mishra, \{Neeraj Kumar\} and Kim, \{In Su\}",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

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doi = "10.1016/j.tetlet.2018.09.025",

language = "English",

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T1 - Site-selective C–H nitration of N-aryl-7-azaindoles under palladium(II) catalysis

AU - Chun, Rina

AU - Kim, Saegun

AU - Han, Sang Hoon

AU - Pandey, Ashok Kumar

AU - Mishra, Neeraj Kumar

AU - Kim, In Su

PY - 2018/10/24

Y1 - 2018/10/24

N2 - The site-selective C–H nitration reaction of 7-azaindoles with t-butyl nitrite under palladium catalysis is described. This protocol provides an efficient method for the construction of ortho-nitrated N-aryl-7-azaindoles with excellent site-selectivity and functional group compatibility. The formed 7-azaindole derivatives can be readily transformed into 7-azaindoles containing an aniline functional group under palladium-catalyzed hydrogenation conditions.

AB - The site-selective C–H nitration reaction of 7-azaindoles with t-butyl nitrite under palladium catalysis is described. This protocol provides an efficient method for the construction of ortho-nitrated N-aryl-7-azaindoles with excellent site-selectivity and functional group compatibility. The formed 7-azaindole derivatives can be readily transformed into 7-azaindoles containing an aniline functional group under palladium-catalyzed hydrogenation conditions.

KW - Azaindoles

KW - C–H functionalization

KW - Nitration

KW - Palladium

KW - Regioselectivity

UR - https://www.scopus.com/pages/publications/85054011366

U2 - 10.1016/j.tetlet.2018.09.025

DO - 10.1016/j.tetlet.2018.09.025

M3 - Article

AN - SCOPUS:85054011366

SN - 0040-4039

VL - 59

SP - 3848

EP - 3852

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -

Site-selective C–H nitration of N-aryl-7-azaindoles under palladium(II) catalysis

Abstract

Keywords

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