Catalytic method for the synthesis of C-N-linked BI(HETEROARYL)S using heteroaryl ethers and N -Benzoyl heteroarenes

Saori Tanii; Mieko Arisawa; Takaya Tougo; Masahiko Yamaguchi

doi:10.1021/acs.orglett.8b00245

Catalytic method for the synthesis of C-N-linked BI(HETEROARYL)S using heteroaryl ethers and N -Benzoyl heteroarenes

Saori Tanii, Mieko Arisawa, Takaya Tougo, Masahiko Yamaguchi

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

9 Citations (Scopus)

Abstract

C-N-linked bi(heteroaryl)s are synthesized by a rhodium-catalyzed N-heteroarylation reaction of N-benzoyl heteroarenes including azoles/azolones, pyridones, cyclic ureas, and cyclic imides using heteroaryl aryl ethers. The reaction involves the covalent bond-exchange reaction of N-CO and HetAr-O bonds without using metal bases and exhibits a broad applicability, giving diverse C-N-linked bi(heteroaryl)s containing five- and six-membered heteroarenes. The N-heteroarylation of N-H azoles/azolones and pyridone proceeds at higher reaction temperatures.

Original language	English
Pages (from-to)	1756-1759
Number of pages	4
Journal	Organic letters
Volume	20
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.8b00245
Publication status	Published - Apr 6 2018
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b00245

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title = "Catalytic method for the synthesis of C-N-linked BI(HETEROARYL)S using heteroaryl ethers and N -Benzoyl heteroarenes",

abstract = "C-N-linked bi(heteroaryl)s are synthesized by a rhodium-catalyzed N-heteroarylation reaction of N-benzoyl heteroarenes including azoles/azolones, pyridones, cyclic ureas, and cyclic imides using heteroaryl aryl ethers. The reaction involves the covalent bond-exchange reaction of N-CO and HetAr-O bonds without using metal bases and exhibits a broad applicability, giving diverse C-N-linked bi(heteroaryl)s containing five- and six-membered heteroarenes. The N-heteroarylation of N-H azoles/azolones and pyridone proceeds at higher reaction temperatures.",

author = "Saori Tanii and Mieko Arisawa and Takaya Tougo and Masahiko Yamaguchi",

note = "Funding Information: This research was supported by the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED), JSPS KAKENHI Grant Nos. 17K19112 and 15H00911, and Tohoku University Center for Gender Equality Promotion (TUMUG). Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = apr,

day = "6",

doi = "10.1021/acs.orglett.8b00245",

language = "English",

volume = "20",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Catalytic method for the synthesis of C-N-linked BI(HETEROARYL)S using heteroaryl ethers and N -Benzoyl heteroarenes

AU - Tanii, Saori

AU - Arisawa, Mieko

AU - Tougo, Takaya

AU - Yamaguchi, Masahiko

N1 - Funding Information: This research was supported by the Platform Project for Supporting Drug Discovery and Life Science Research funded by Japan Agency for Medical Research and Development (AMED), JSPS KAKENHI Grant Nos. 17K19112 and 15H00911, and Tohoku University Center for Gender Equality Promotion (TUMUG). Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/4/6

Y1 - 2018/4/6

N2 - C-N-linked bi(heteroaryl)s are synthesized by a rhodium-catalyzed N-heteroarylation reaction of N-benzoyl heteroarenes including azoles/azolones, pyridones, cyclic ureas, and cyclic imides using heteroaryl aryl ethers. The reaction involves the covalent bond-exchange reaction of N-CO and HetAr-O bonds without using metal bases and exhibits a broad applicability, giving diverse C-N-linked bi(heteroaryl)s containing five- and six-membered heteroarenes. The N-heteroarylation of N-H azoles/azolones and pyridone proceeds at higher reaction temperatures.

AB - C-N-linked bi(heteroaryl)s are synthesized by a rhodium-catalyzed N-heteroarylation reaction of N-benzoyl heteroarenes including azoles/azolones, pyridones, cyclic ureas, and cyclic imides using heteroaryl aryl ethers. The reaction involves the covalent bond-exchange reaction of N-CO and HetAr-O bonds without using metal bases and exhibits a broad applicability, giving diverse C-N-linked bi(heteroaryl)s containing five- and six-membered heteroarenes. The N-heteroarylation of N-H azoles/azolones and pyridone proceeds at higher reaction temperatures.

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Catalytic method for the synthesis of C-N-linked BI(HETEROARYL)S using heteroaryl ethers and N -Benzoyl heteroarenes

Abstract

All Science Journal Classification (ASJC) codes

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