Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems

Faiyaz Khan; Michael Dlugosch; Xin Liu; Marium Khan; Martin G. Banwell; Jas S. Ward; Paul D. Carr

doi:10.1021/acs.orglett.8b01015

Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems

Faiyaz Khan, Michael Dlugosch, Xin Liu, Marium Khan, Martin G. Banwell^*, Jas S. Ward, Paul D. Carr

^*Corresponding author for this work

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

15 Citations (Scopus)

Abstract

The palladium-catalyzed Ullmann cross-coupling of β-iodoenones and β-iodoacrylates such as 5 (X = I) with o-halonitroarenes and o-iodobenzonitriles including 2 affords products such as compound 7. These can be engaged in a range of reductive cyclization reactions leading to heterocyclic frameworks such as 3,4-benzomorphan derivative 43.

Original language	English
Pages (from-to)	2770-2773
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.8b01015
Publication status	Published - 4 May 2018

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Khan, F., Dlugosch, M., Liu, X., Khan, M., Banwell, M. G., Ward, J. S., & Carr, P. D. (2018). Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems. Organic Letters, 20(9), 2770-2773. https://doi.org/10.1021/acs.orglett.8b01015

@article{a03baa47abb24453b236cbdc69a0cd16,

title = "Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems",

abstract = "The palladium-catalyzed Ullmann cross-coupling of β-iodoenones and β-iodoacrylates such as 5 (X = I) with o-halonitroarenes and o-iodobenzonitriles including 2 affords products such as compound 7. These can be engaged in a range of reductive cyclization reactions leading to heterocyclic frameworks such as 3,4-benzomorphan derivative 43.",

author = "Faiyaz Khan and Michael Dlugosch and Xin Liu and Marium Khan and Banwell, {Martin G.} and Ward, {Jas S.} and Carr, {Paul D.}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = may,

day = "4",

doi = "10.1021/acs.orglett.8b01015",

language = "English",

volume = "20",

pages = "2770--2773",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "9",

}

Khan, F, Dlugosch, M, Liu, X, Khan, M, Banwell, MG, Ward, JS & Carr, PD 2018, 'Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems', Organic Letters, vol. 20, no. 9, pp. 2770-2773. https://doi.org/10.1021/acs.orglett.8b01015

Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems. / Khan, Faiyaz; Dlugosch, Michael; Liu, Xin et al.
In: Organic Letters, Vol. 20, No. 9, 04.05.2018, p. 2770-2773.

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

TY - JOUR

T1 - Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems

AU - Khan, Faiyaz

AU - Dlugosch, Michael

AU - Liu, Xin

AU - Khan, Marium

AU - Banwell, Martin G.

AU - Ward, Jas S.

AU - Carr, Paul D.

PY - 2018/5/4

Y1 - 2018/5/4

N2 - The palladium-catalyzed Ullmann cross-coupling of β-iodoenones and β-iodoacrylates such as 5 (X = I) with o-halonitroarenes and o-iodobenzonitriles including 2 affords products such as compound 7. These can be engaged in a range of reductive cyclization reactions leading to heterocyclic frameworks such as 3,4-benzomorphan derivative 43.

AB - The palladium-catalyzed Ullmann cross-coupling of β-iodoenones and β-iodoacrylates such as 5 (X = I) with o-halonitroarenes and o-iodobenzonitriles including 2 affords products such as compound 7. These can be engaged in a range of reductive cyclization reactions leading to heterocyclic frameworks such as 3,4-benzomorphan derivative 43.

UR - http://www.scopus.com/inward/record.url?scp=85046700000&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b01015

DO - 10.1021/acs.orglett.8b01015

M3 - Article

SN - 1523-7060

VL - 20

SP - 2770

EP - 2773

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Palladium-Catalyzed Ullmann Cross-Coupling of β-Iodoenones and β-Iodoacrylates with o-Halonitroarenes or o-Iodobenzonitriles and Reductive Cyclization of the Resulting Products to Give Diverse Heterocyclic Systems

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