Chemoselective reduction of quinols as an alternative to Sonogashira coupling: Synthesis of polysubstituted benzofurans

Youngeun Jung; Ikyon Kim

doi:10.1039/c6ob01941b

Chemoselective reduction of quinols as an alternative to Sonogashira coupling: Synthesis of polysubstituted benzofurans

Youngeun Jung, Ikyon Kim

Department of Pharmacy

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

12 Citations (Scopus)

Abstract

An efficient synthetic approach to polysubstituted benzofurans is described, using 2-methoxyquinone as a benzofuran backbone. Nucleophilic addition of terminal alkynes to 2-methoxy-1,4-benzoquinone afforded the corresponding quinols containing an alkyne unit, which were converted to phenols via mild Zn-mediated reduction. After proper protection of the free phenolic OH, 5-endo-dig iodocyclization allowed facile access to a number of 3-iodobenzofurans. In addition, it was demonstrated for the first time that o-methoxyarylalkynes underwent intramolecular hydroalkoxylation under the influence of AgOTf furnishing the corresponding benzofurans.

Original language	English
Pages (from-to)	10454-10472
Number of pages	19
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	44
DOIs	https://doi.org/10.1039/c6ob01941b
Publication status	Published - 2016

Bibliographical note

Funding Information:
This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2014R1A2A1A11050491).

Publisher Copyright:
© 2016 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/c6ob01941b

Cite this

@article{9cdbbb365aec4f5682df94cc03296ae0,

title = "Chemoselective reduction of quinols as an alternative to Sonogashira coupling: Synthesis of polysubstituted benzofurans",

abstract = "An efficient synthetic approach to polysubstituted benzofurans is described, using 2-methoxyquinone as a benzofuran backbone. Nucleophilic addition of terminal alkynes to 2-methoxy-1,4-benzoquinone afforded the corresponding quinols containing an alkyne unit, which were converted to phenols via mild Zn-mediated reduction. After proper protection of the free phenolic OH, 5-endo-dig iodocyclization allowed facile access to a number of 3-iodobenzofurans. In addition, it was demonstrated for the first time that o-methoxyarylalkynes underwent intramolecular hydroalkoxylation under the influence of AgOTf furnishing the corresponding benzofurans.",

author = "Youngeun Jung and Ikyon Kim",

note = "Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2014R1A2A1A11050491). Publisher Copyright: {\textcopyright} 2016 The Royal Society of Chemistry.",

year = "2016",

doi = "10.1039/c6ob01941b",

language = "English",

volume = "14",

pages = "10454--10472",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "44",

}

TY - JOUR

T1 - Chemoselective reduction of quinols as an alternative to Sonogashira coupling

T2 - Synthesis of polysubstituted benzofurans

AU - Jung, Youngeun

AU - Kim, Ikyon

N1 - Funding Information: This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIP) (2014R1A2A1A11050491). Publisher Copyright: © 2016 The Royal Society of Chemistry.

PY - 2016

Y1 - 2016

N2 - An efficient synthetic approach to polysubstituted benzofurans is described, using 2-methoxyquinone as a benzofuran backbone. Nucleophilic addition of terminal alkynes to 2-methoxy-1,4-benzoquinone afforded the corresponding quinols containing an alkyne unit, which were converted to phenols via mild Zn-mediated reduction. After proper protection of the free phenolic OH, 5-endo-dig iodocyclization allowed facile access to a number of 3-iodobenzofurans. In addition, it was demonstrated for the first time that o-methoxyarylalkynes underwent intramolecular hydroalkoxylation under the influence of AgOTf furnishing the corresponding benzofurans.

AB - An efficient synthetic approach to polysubstituted benzofurans is described, using 2-methoxyquinone as a benzofuran backbone. Nucleophilic addition of terminal alkynes to 2-methoxy-1,4-benzoquinone afforded the corresponding quinols containing an alkyne unit, which were converted to phenols via mild Zn-mediated reduction. After proper protection of the free phenolic OH, 5-endo-dig iodocyclization allowed facile access to a number of 3-iodobenzofurans. In addition, it was demonstrated for the first time that o-methoxyarylalkynes underwent intramolecular hydroalkoxylation under the influence of AgOTf furnishing the corresponding benzofurans.

UR - http://www.scopus.com/inward/record.url?scp=84994496629&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84994496629&partnerID=8YFLogxK

U2 - 10.1039/c6ob01941b

DO - 10.1039/c6ob01941b

M3 - Article

AN - SCOPUS:84994496629

SN - 1477-0520

VL - 14

SP - 10454

EP - 10472

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 44

ER -

Chemoselective reduction of quinols as an alternative to Sonogashira coupling: Synthesis of polysubstituted benzofurans

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this