Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketonest

Alexander V. Kel'in, Vladimir Gevorgyan

Research output: Contribution to journalArticle

197 Citations (Scopus)

Abstract

A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

Original languageEnglish (US)
Pages (from-to)95-98
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number1
DOIs
StatePublished - Jan 11 2002
Externally publishedYes

Fingerprint

Furans
Ketones
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketonest. / Kel'in, Alexander V.; Gevorgyan, Vladimir.

In: Journal of Organic Chemistry, Vol. 67, No. 1, 11.01.2002, p. 95-98.

Research output: Contribution to journalArticle

@article{cf456ad311e54dacb89dc2d866816a78,
title = "Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketonest",
abstract = "A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.",
author = "Kel'in, {Alexander V.} and Vladimir Gevorgyan",
year = "2002",
month = "1",
day = "11",
doi = "10.1021/jo010832v",
language = "English (US)",
volume = "67",
pages = "95--98",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "1",

}

TY - JOUR

T1 - Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketonest

AU - Kel'in, Alexander V.

AU - Gevorgyan, Vladimir

PY - 2002/1/11

Y1 - 2002/1/11

N2 - A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

AB - A mild, general, and efficient method for the synthesis of 2-monosubstituted and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones was developed. It was demonstrated that furans containing both acid- and base-labile groups could be easily synthesized using this methodology. A plausible mechanism for this transformation is proposed.

UR - http://www.scopus.com/inward/record.url?scp=0037059436&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037059436&partnerID=8YFLogxK

U2 - 10.1021/jo010832v

DO - 10.1021/jo010832v

M3 - Article

C2 - 11777444

AN - SCOPUS:0037059436

VL - 67

SP - 95

EP - 98

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 1

ER -