Synthesis of unsymmetric HetAr-X-HetAr' compounds by rhodium-catalyzed heteroaryl exchange reactions

Mieko Arisawa; Saori Tanii; Takeru Tazawa; Masahiko Yamaguchi

doi:10.3987/REV-17-869

Synthesis of unsymmetric HetAr-X-HetAr' compounds by rhodium-catalyzed heteroaryl exchange reactions

Mieko Arisawa, Saori Tanii, Takeru Tazawa, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

8 Citations (Scopus)

Abstract

Unsymmetric HetAr-X-HetAr' compounds have flexible and chiral structures, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Unsymmetric HetAr-X-HetAr' compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. By using this method, unsymmetric HetAr-O-HetAr', HetAr-S-HetAr', and HetAr-CH₂-HetAr' compounds as well as HetAr-F compounds were obtained from heteroaryl aryl ethers and various heteroaryl reagents. The rhodium-catalyzed synthesis has a broad applicability, which gives novel unsymmetric HetAr-X-HetAr' compounds containing five- and six-membered heteroarenes.

Original language	English
Pages (from-to)	2179-2207
Number of pages	29
Journal	Heterocycles
Volume	94
Issue number	12
DOIs	https://doi.org/10.3987/REV-17-869
Publication status	Published - 2017

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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@article{42ed8d06ce44489788797db8c8d95db6,

title = "Synthesis of unsymmetric HetAr-X-HetAr' compounds by rhodium-catalyzed heteroaryl exchange reactions",

abstract = "Unsymmetric HetAr-X-HetAr' compounds have flexible and chiral structures, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Unsymmetric HetAr-X-HetAr' compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. By using this method, unsymmetric HetAr-O-HetAr', HetAr-S-HetAr', and HetAr-CH2-HetAr' compounds as well as HetAr-F compounds were obtained from heteroaryl aryl ethers and various heteroaryl reagents. The rhodium-catalyzed synthesis has a broad applicability, which gives novel unsymmetric HetAr-X-HetAr' compounds containing five- and six-membered heteroarenes.",

author = "Mieko Arisawa and Saori Tanii and Takeru Tazawa and Masahiko Yamaguchi",

note = "Funding Information: The research reviewed in this paper was possible only through the enthusiasm and creativity of all co-workers, whose names are acknowledged on the publications from our laboratory cited here. 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 Numbers 17K19112, 15H00911, Tohoku University Center for Gender Equality Promotion (TUMUG), and Morinomiyako Project for Empowering Women in Research.",

year = "2017",

doi = "10.3987/REV-17-869",

language = "English",

volume = "94",

pages = "2179--2207",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

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AU - Arisawa, Mieko

AU - Tanii, Saori

AU - Tazawa, Takeru

AU - Yamaguchi, Masahiko

N1 - Funding Information: The research reviewed in this paper was possible only through the enthusiasm and creativity of all co-workers, whose names are acknowledged on the publications from our laboratory cited here. 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 Numbers 17K19112, 15H00911, Tohoku University Center for Gender Equality Promotion (TUMUG), and Morinomiyako Project for Empowering Women in Research.

PY - 2017

Y1 - 2017

N2 - Unsymmetric HetAr-X-HetAr' compounds have flexible and chiral structures, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Unsymmetric HetAr-X-HetAr' compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. By using this method, unsymmetric HetAr-O-HetAr', HetAr-S-HetAr', and HetAr-CH2-HetAr' compounds as well as HetAr-F compounds were obtained from heteroaryl aryl ethers and various heteroaryl reagents. The rhodium-catalyzed synthesis has a broad applicability, which gives novel unsymmetric HetAr-X-HetAr' compounds containing five- and six-membered heteroarenes.

AB - Unsymmetric HetAr-X-HetAr' compounds have flexible and chiral structures, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Unsymmetric HetAr-X-HetAr' compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. By using this method, unsymmetric HetAr-O-HetAr', HetAr-S-HetAr', and HetAr-CH2-HetAr' compounds as well as HetAr-F compounds were obtained from heteroaryl aryl ethers and various heteroaryl reagents. The rhodium-catalyzed synthesis has a broad applicability, which gives novel unsymmetric HetAr-X-HetAr' compounds containing five- and six-membered heteroarenes.

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JO - Heterocycles

JF - Heterocycles

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Synthesis of unsymmetric HetAr-X-HetAr' compounds by rhodium-catalyzed heteroaryl exchange reactions

Abstract

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