Rhodium-Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides

Mieko Arisawa; Ren Suzuki; Keiichiro Ohashi; Masahiko Yamaguchi

doi:10.1002/ajoc.202000077

Rhodium-Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides

Mieko Arisawa, Ren Suzuki, Keiichiro Ohashi, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

2 Citations (Scopus)

Abstract

A rhodium complex catalyzed C−Se bond formation between diheteroaryl diselenides and acid fluorides in the presence of triphenylphosphine to provide heteroarylselenyl esters in good yields. The reaction was applicable to five- and six-membered heteroaryl compounds. The heteroarylselenyl esters can be used as heteroaryselenating reagents in the synthesis of heteroaryl selenides, as shown by a platinum-catalyzed addition reaction with 1-octyne.

Original language	English
Pages (from-to)	553-556
Number of pages	4
Journal	Asian Journal of Organic Chemistry
Volume	9
Issue number	4
DOIs	https://doi.org/10.1002/ajoc.202000077
Publication status	Published - 2020 Apr 1

Keywords

Acid fluorides
C−Se bond formation
Diheteroaryl diselenides
Heteroarylselenyl esters
Heteroaryselenating reagents

ASJC Scopus subject areas

Organic Chemistry

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10.1002/ajoc.202000077

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title = "Rhodium-Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides",

abstract = "A rhodium complex catalyzed C−Se bond formation between diheteroaryl diselenides and acid fluorides in the presence of triphenylphosphine to provide heteroarylselenyl esters in good yields. The reaction was applicable to five- and six-membered heteroaryl compounds. The heteroarylselenyl esters can be used as heteroaryselenating reagents in the synthesis of heteroaryl selenides, as shown by a platinum-catalyzed addition reaction with 1-octyne.",

keywords = "Acid fluorides, C−Se bond formation, Diheteroaryl diselenides, Heteroarylselenyl esters, Heteroaryselenating reagents",

author = "Mieko Arisawa and Ren Suzuki and Keiichiro Ohashi and Masahiko Yamaguchi",

note = "Funding Information: This research was supported by the Platform Project for Supporting Drug Discovery and Life Science Research from AMED (Grant Number JP19am0101100) and Tohoku University Center for Gender Equality Promotion (TUMUG). Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ajoc.202000077",

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T1 - Rhodium-Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides

AU - Arisawa, Mieko

AU - Suzuki, Ren

AU - Ohashi, Keiichiro

AU - Yamaguchi, Masahiko

N1 - Funding Information: This research was supported by the Platform Project for Supporting Drug Discovery and Life Science Research from AMED (Grant Number JP19am0101100) and Tohoku University Center for Gender Equality Promotion (TUMUG). Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2020/4/1

Y1 - 2020/4/1

N2 - A rhodium complex catalyzed C−Se bond formation between diheteroaryl diselenides and acid fluorides in the presence of triphenylphosphine to provide heteroarylselenyl esters in good yields. The reaction was applicable to five- and six-membered heteroaryl compounds. The heteroarylselenyl esters can be used as heteroaryselenating reagents in the synthesis of heteroaryl selenides, as shown by a platinum-catalyzed addition reaction with 1-octyne.

AB - A rhodium complex catalyzed C−Se bond formation between diheteroaryl diselenides and acid fluorides in the presence of triphenylphosphine to provide heteroarylselenyl esters in good yields. The reaction was applicable to five- and six-membered heteroaryl compounds. The heteroarylselenyl esters can be used as heteroaryselenating reagents in the synthesis of heteroaryl selenides, as shown by a platinum-catalyzed addition reaction with 1-octyne.

KW - Acid fluorides

KW - C−Se bond formation

KW - Diheteroaryl diselenides

KW - Heteroarylselenyl esters

KW - Heteroaryselenating reagents

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JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

SN - 2193-5807

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Rhodium-Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides

Abstract

Keywords

ASJC Scopus subject areas

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