Construction of β-Haloenamides via Direct Copper-Promoted Coupling of Lactams with 2-Chloro and 2-Bromo Vinyliodides

Cuixiang Sun; Jason E. Camp; Steven M. Weinreb

doi:10.1021/ol060093a

Construction of β-Haloenamides via Direct Copper-Promoted Coupling of Lactams with 2-Chloro and 2-Bromo Vinyliodides

Cuixiang Sun, Jason E. Camp, Steven M. Weinreb

Department of Chemistry

Pennsylvania State University

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

62 Citations (SciVal)

Abstract

Cu(I)-catalyzed coupling of lactams with (E)-2-chlorovinyl iodides or (E)-2-bromovinyl iodides produces the corresponding β-halo enamides in moderate to excellent yields. E.g., in the presence of CuI and MeNHCH2CH2NHMe, coupling of (E)-2-chlorovinyl iodide I with lactam II gave 43% β-halo enamide III.

Original language	English
Pages (from-to)	1779-1781
Number of pages	3
Journal	Organic Letters
Volume	8
Issue number	9
Early online date	30 Mar 2006
DOIs	https://doi.org/10.1021/ol060093a
Publication status	Published - 2006

Bibliographical note

M1 - Copyright (C) 2018 American Chemical Society (ACS). All Rights Reserved.

CAPLUS AN 2006:291636(Journal)

Keywords

halo enamide prepn
copper catalyst coupling lactam chlorovinyl bromovinyl iodide

Access to Document

10.1021/ol060093a

Cite this

@article{6212b6aeeace4a10bcbedddd27847bfe,

title = "Construction of β-Haloenamides via Direct Copper-Promoted Coupling of Lactams with 2-Chloro and 2-Bromo Vinyliodides",

abstract = "Cu(I)-catalyzed coupling of lactams with (E)-2-chlorovinyl iodides or (E)-2-bromovinyl iodides produces the corresponding β-halo enamides in moderate to excellent yields. E.g., in the presence of CuI and MeNHCH2CH2NHMe, coupling of (E)-2-chlorovinyl iodide I with lactam II gave 43\% β-halo enamide III.",

keywords = "halo enamide prepn, copper catalyst coupling lactam chlorovinyl bromovinyl iodide",

author = "Cuixiang Sun and Camp, \{Jason E.\} and Weinreb, \{Steven M.\}",

year = "2006",

doi = "10.1021/ol060093a",

language = "English",

volume = "8",

pages = "1779--1781",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Construction of β-Haloenamides via Direct Copper-Promoted Coupling of Lactams with 2-Chloro and 2-Bromo Vinyliodides

AU - Sun, Cuixiang

AU - Camp, Jason E.

AU - Weinreb, Steven M.

PY - 2006

Y1 - 2006

N2 - Cu(I)-catalyzed coupling of lactams with (E)-2-chlorovinyl iodides or (E)-2-bromovinyl iodides produces the corresponding β-halo enamides in moderate to excellent yields. E.g., in the presence of CuI and MeNHCH2CH2NHMe, coupling of (E)-2-chlorovinyl iodide I with lactam II gave 43% β-halo enamide III.

AB - Cu(I)-catalyzed coupling of lactams with (E)-2-chlorovinyl iodides or (E)-2-bromovinyl iodides produces the corresponding β-halo enamides in moderate to excellent yields. E.g., in the presence of CuI and MeNHCH2CH2NHMe, coupling of (E)-2-chlorovinyl iodide I with lactam II gave 43% β-halo enamide III.

KW - halo enamide prepn

KW - copper catalyst coupling lactam chlorovinyl bromovinyl iodide

UR - https://www.scopus.com/pages/publications/33646459483

U2 - 10.1021/ol060093a

DO - 10.1021/ol060093a

M3 - Article

SN - 1523-7060

VL - 8

SP - 1779

EP - 1781

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Construction of β-Haloenamides via Direct Copper-Promoted Coupling of Lactams with 2-Chloro and 2-Bromo Vinyliodides

Abstract

Bibliographical note

Keywords

Access to Document

Other files and links

Fingerprint

Cite this