Sequential copper-catalyzed vinylation/ cyclization: An efficient synthesis of functionalized oxazoles

Rubén Martín; Ana Cuenca; Stephen L. Buchwald

doi:10.1021/ol7024718

Sequential copper-catalyzed vinylation/ cyclization: An efficient synthesis of functionalized oxazoles

Rubén Martín
, Ana Cuenca
, Stephen L. Buchwald^*

^*Corresponding author for this work

Research output: Indexed journal article › Article › peer-review

139 Citations (Scopus)

Abstract

A modular and practical synthesis of highly substituted oxazoles has been developed. The transformation consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.

Original language	English
Pages (from-to)	5521-5524
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	26
DOIs	https://doi.org/10.1021/ol7024718
Publication status	Published - 20 Dec 2007
Externally published	Yes

Keywords

C-n
Primary amides
Cyclization
Conversion
Amidation
Imidazole
Enamides
Ullmann

Access to Document

10.1021/ol7024718

Cite this

@article{061790f4e61c4bcb8129c1b631d6afa4,

title = "Sequential copper-catalyzed vinylation/ cyclization: An efficient synthesis of functionalized oxazoles",

abstract = "A modular and practical synthesis of highly substituted oxazoles has been developed. The transformation consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.",

keywords = "C-n, Primary amides, Cyclization, Conversion, Amidation, Imidazole, Enamides, Ullmann",

author = "Rub{\'e}n Mart{\'i}n and Ana Cuenca and Buchwald, \{Stephen L.\}",

year = "2007",

month = dec,

day = "20",

doi = "10.1021/ol7024718",

language = "English",

volume = "9",

pages = "5521--5524",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "26",

}

TY - JOUR

T1 - Sequential copper-catalyzed vinylation/ cyclization

T2 - An efficient synthesis of functionalized oxazoles

AU - Martín, Rubén

AU - Cuenca, Ana

AU - Buchwald, Stephen L.

PY - 2007/12/20

Y1 - 2007/12/20

N2 - A modular and practical synthesis of highly substituted oxazoles has been developed. The transformation consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.

AB - A modular and practical synthesis of highly substituted oxazoles has been developed. The transformation consists of a sequential copper-catalyzed amidation of vinyl halides followed by cyclization promoted by iodine. A wide variety of functionalized oxazoles and polyazoles can be obtained in a selective manner from simple and easily accessible precursors.

KW - C-n

KW - Primary amides

KW - Cyclization

KW - Conversion

KW - Amidation

KW - Imidazole

KW - Enamides

KW - Ullmann

UR - https://www.scopus.com/pages/publications/38349086723

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000251614900048&DestLinkType=FullRecord&DestApp=WOS

U2 - 10.1021/ol7024718

DO - 10.1021/ol7024718

M3 - Article

C2 - 18020351

AN - SCOPUS:38349086723

SN - 1523-7060

VL - 9

SP - 5521

EP - 5524

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

Sequential copper-catalyzed vinylation/ cyclization: An efficient synthesis of functionalized oxazoles

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this