A mild two-step propargylation of aromatic bioactive small molecules

Naoki Kanoh; Toshitaka Okamura; Takahiro Suzuki; Yoshiharu Iwabuchi

doi:10.1039/c7ob01587a

A mild two-step propargylation of aromatic bioactive small molecules

Naoki Kanoh, Toshitaka Okamura, Takahiro Suzuki, Yoshiharu Iwabuchi

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

6 Citations (Scopus)

Abstract

A two-step method for introducing a propargyl group in aromatic bioactive small molecules has been developed. This method features propargylation of aromatic groups using a cationic propargyl hexacarbonyl complex in the presence of cesium carbonate, and decomplexation of the resultant cobalt complexes using 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. These reactions proceed under mild conditions, and thus are applicable for acid- and/or oxidant-sensitive aromatic bioactive small molecules.

Original language	English
Pages (from-to)	7190-7195
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	34
DOIs	https://doi.org/10.1039/c7ob01587a
Publication status	Published - 2017
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c7ob01587a

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title = "A mild two-step propargylation of aromatic bioactive small molecules",

abstract = "A two-step method for introducing a propargyl group in aromatic bioactive small molecules has been developed. This method features propargylation of aromatic groups using a cationic propargyl hexacarbonyl complex in the presence of cesium carbonate, and decomplexation of the resultant cobalt complexes using 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. These reactions proceed under mild conditions, and thus are applicable for acid- and/or oxidant-sensitive aromatic bioactive small molecules.",

author = "Naoki Kanoh and Toshitaka Okamura and Takahiro Suzuki and Yoshiharu Iwabuchi",

note = "Funding Information: This work was partially supported by The Naito Foundation, by a Grant-in-Aid for Scientific Research on the Innovative Area “Chemical Biology of Natural Products” (no. 23102013 to NK) from The Ministry of Education, Culture, Sports, Science, and Technology of Japan, and by the Platform Project for Supporting Drug Discovery and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) from the Japan Agency for Medical Research and Development (AMED). Publisher Copyright: {\textcopyright} 2017 The Royal Society of Chemistry.",

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AU - Kanoh, Naoki

AU - Okamura, Toshitaka

AU - Suzuki, Takahiro

AU - Iwabuchi, Yoshiharu

N1 - Funding Information: This work was partially supported by The Naito Foundation, by a Grant-in-Aid for Scientific Research on the Innovative Area “Chemical Biology of Natural Products” (no. 23102013 to NK) from The Ministry of Education, Culture, Sports, Science, and Technology of Japan, and by the Platform Project for Supporting Drug Discovery and Life Science Research (Platform for Drug Discovery, Informatics, and Structural Life Science) from the Japan Agency for Medical Research and Development (AMED). Publisher Copyright: © 2017 The Royal Society of Chemistry.

PY - 2017

Y1 - 2017

N2 - A two-step method for introducing a propargyl group in aromatic bioactive small molecules has been developed. This method features propargylation of aromatic groups using a cationic propargyl hexacarbonyl complex in the presence of cesium carbonate, and decomplexation of the resultant cobalt complexes using 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. These reactions proceed under mild conditions, and thus are applicable for acid- and/or oxidant-sensitive aromatic bioactive small molecules.

AB - A two-step method for introducing a propargyl group in aromatic bioactive small molecules has been developed. This method features propargylation of aromatic groups using a cationic propargyl hexacarbonyl complex in the presence of cesium carbonate, and decomplexation of the resultant cobalt complexes using 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. These reactions proceed under mild conditions, and thus are applicable for acid- and/or oxidant-sensitive aromatic bioactive small molecules.

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A mild two-step propargylation of aromatic bioactive small molecules

Abstract

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