Ru(II)-Catalyzed C-H Aminocarbonylation of N -(Hetero)aryl-7-azaindoles with Isocyanates

Taejoo Jeong; Suk Hun Lee; Rina Chun; Sangil Han; Sang Hoon Han; Yeong Uk Jeon; Jihye Park; Takehiko Yoshimitsu; Neeraj Kumar Mishra; In Su Kim

doi:10.1021/acs.joc.8b00388

Ru(II)-Catalyzed C-H Aminocarbonylation of N -(Hetero)aryl-7-azaindoles with Isocyanates

Taejoo Jeong, Suk Hun Lee, Rina Chun, Sangil Han, Sang Hoon Han, Yeong Uk Jeon, Jihye Park, Takehiko Yoshimitsu, Neeraj Kumar Mishra, In Su Kim

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

22 Citations (Scopus)

Abstract

The ruthenium(II)-catalyzed C-H aminocarbonylation of N-(hetero)aryl-7-azaindoles with isocyanates is described. The excellent site selectivity at the ortho-position within the N-(hetero)aryl ring was observed to provide ortho-amidated N-(hetero)aryl-7-azaindoles under the mild reaction conditions. The resulting 7-azaindole derivatives can be readily transformed into 7-azaindoles containing carboxylic acid and alkyl amine functional groups.

Original language	English
Pages (from-to)	4641-4649
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	83
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.8b00388
Publication status	Published - Apr 20 2018

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1021/acs.joc.8b00388

Cite this

@article{d11b1476fe4246f48597596e930496fe,

title = "Ru(II)-Catalyzed C-H Aminocarbonylation of N -(Hetero)aryl-7-azaindoles with Isocyanates",

abstract = "The ruthenium(II)-catalyzed C-H aminocarbonylation of N-(hetero)aryl-7-azaindoles with isocyanates is described. The excellent site selectivity at the ortho-position within the N-(hetero)aryl ring was observed to provide ortho-amidated N-(hetero)aryl-7-azaindoles under the mild reaction conditions. The resulting 7-azaindole derivatives can be readily transformed into 7-azaindoles containing carboxylic acid and alkyl amine functional groups.",

author = "Taejoo Jeong and Lee, {Suk Hun} and Rina Chun and Sangil Han and Han, {Sang Hoon} and Jeon, {Yeong Uk} and Jihye Park and Takehiko Yoshimitsu and Mishra, {Neeraj Kumar} and Kim, {In Su}",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2016R1A4A1011189, 2017R1D1A1A09000574, and 2017R1A2B2004786). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = apr,

day = "20",

doi = "10.1021/acs.joc.8b00388",

language = "English",

volume = "83",

pages = "4641--4649",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Ru(II)-Catalyzed C-H Aminocarbonylation of N -(Hetero)aryl-7-azaindoles with Isocyanates

AU - Jeong, Taejoo

AU - Lee, Suk Hun

AU - Chun, Rina

AU - Han, Sangil

AU - Han, Sang Hoon

AU - Jeon, Yeong Uk

AU - Park, Jihye

AU - Yoshimitsu, Takehiko

AU - Mishra, Neeraj Kumar

AU - Kim, In Su

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2016R1A4A1011189, 2017R1D1A1A09000574, and 2017R1A2B2004786). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/4/20

Y1 - 2018/4/20

N2 - The ruthenium(II)-catalyzed C-H aminocarbonylation of N-(hetero)aryl-7-azaindoles with isocyanates is described. The excellent site selectivity at the ortho-position within the N-(hetero)aryl ring was observed to provide ortho-amidated N-(hetero)aryl-7-azaindoles under the mild reaction conditions. The resulting 7-azaindole derivatives can be readily transformed into 7-azaindoles containing carboxylic acid and alkyl amine functional groups.

AB - The ruthenium(II)-catalyzed C-H aminocarbonylation of N-(hetero)aryl-7-azaindoles with isocyanates is described. The excellent site selectivity at the ortho-position within the N-(hetero)aryl ring was observed to provide ortho-amidated N-(hetero)aryl-7-azaindoles under the mild reaction conditions. The resulting 7-azaindole derivatives can be readily transformed into 7-azaindoles containing carboxylic acid and alkyl amine functional groups.

UR - http://www.scopus.com/inward/record.url?scp=85045750506&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85045750506&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b00388

DO - 10.1021/acs.joc.8b00388

M3 - Article

C2 - 29616808

AN - SCOPUS:85045750506

VL - 83

SP - 4641

EP - 4649

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 8

ER -

Ru(II)-Catalyzed C-H Aminocarbonylation of N -(Hetero)aryl-7-azaindoles with Isocyanates

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this