Synthesis of cycloalkyl/steroidal heteroaryl sulfides using rhodium-catalyzed heteroaryl exchange reaction

Mieko Arisawa; Katsuya Nakai; Tomoki Yamada; Ren Suzuki; Masahiko Yamaguchi

doi:10.3987/COM-19-14147

Synthesis of cycloalkyl/steroidal heteroaryl sulfides using rhodium-catalyzed heteroaryl exchange reaction

Mieko Arisawa, Katsuya Nakai, Tomoki Yamada, Ren Suzuki, Masahiko Yamaguchi

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

1 Citation (Scopus)

Abstract

Cycloalkyl heteroaryl sulfides are efficiently synthesized by the single-bond cleavage and exchange reaction of S-cycloalkyl thioesters and heteroaryl ethers without using a base. The method is applicable to steroids at the A- and D-rings, and provides diverse heteroarylthiolated steroids with five- and six-membered heteroarenes.

Original language	English
Pages (from-to)	104-118
Number of pages	15
Journal	Heterocycles
Volume	100
Issue number	1
DOIs	https://doi.org/10.3987/COM-19-14147
Publication status	Published - 2020
Externally published	Yes

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-19-14147

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title = "Synthesis of cycloalkyl/steroidal heteroaryl sulfides using rhodium-catalyzed heteroaryl exchange reaction",

abstract = "Cycloalkyl heteroaryl sulfides are efficiently synthesized by the single-bond cleavage and exchange reaction of S-cycloalkyl thioesters and heteroaryl ethers without using a base. The method is applicable to steroids at the A- and D-rings, and provides diverse heteroarylthiolated steroids with five- and six-membered heteroarenes.",

author = "Mieko Arisawa and Katsuya Nakai and Tomoki Yamada and Ren Suzuki 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 JP18am0101100) and Tohoku University Center for Gender Equality Promotion (TUMUG). Publisher Copyright: {\textcopyright} 2020 The Japan Institute of Heterocyclic Chemistry.",

year = "2020",

doi = "10.3987/COM-19-14147",

language = "English",

volume = "100",

pages = "104--118",

journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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T1 - Synthesis of cycloalkyl/steroidal heteroaryl sulfides using rhodium-catalyzed heteroaryl exchange reaction

AU - Arisawa, Mieko

AU - Nakai, Katsuya

AU - Yamada, Tomoki

AU - Suzuki, Ren

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 JP18am0101100) and Tohoku University Center for Gender Equality Promotion (TUMUG). Publisher Copyright: © 2020 The Japan Institute of Heterocyclic Chemistry.

PY - 2020

Y1 - 2020

N2 - Cycloalkyl heteroaryl sulfides are efficiently synthesized by the single-bond cleavage and exchange reaction of S-cycloalkyl thioesters and heteroaryl ethers without using a base. The method is applicable to steroids at the A- and D-rings, and provides diverse heteroarylthiolated steroids with five- and six-membered heteroarenes.

AB - Cycloalkyl heteroaryl sulfides are efficiently synthesized by the single-bond cleavage and exchange reaction of S-cycloalkyl thioesters and heteroaryl ethers without using a base. The method is applicable to steroids at the A- and D-rings, and provides diverse heteroarylthiolated steroids with five- and six-membered heteroarenes.

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U2 - 10.3987/COM-19-14147

DO - 10.3987/COM-19-14147

M3 - Article

AN - SCOPUS:85078176190

SN - 0385-5414

VL - 100

SP - 104

EP - 118

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

Synthesis of cycloalkyl/steroidal heteroaryl sulfides using rhodium-catalyzed heteroaryl exchange reaction

Abstract

All Science Journal Classification (ASJC) codes

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