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

17 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
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Ru(II)-Catalyzed C-H Aminocarbonylation of N -(Hetero)aryl-7-azaindoles with Isocyanates. / Jeong, Taejoo; Lee, Suk Hun; Chun, Rina; Han, Sangil; Han, Sang Hoon; Jeon, Yeong Uk; Park, Jihye; Yoshimitsu, Takehiko; Mishra, Neeraj Kumar; Kim, In Su.

In: Journal of Organic Chemistry, Vol. 83, No. 8, 20.04.2018, p. 4641-4649.

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

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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.",

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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.

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

Abstract

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