A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds

Martin G. Banwell; Matthew T. Jones; David T.J. Loong; David W. Lupton; David M. Pinkerton; Jayanta K. Ray; Anthony C. Willis

doi:10.1016/j.tet.2010.09.042

A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds

Martin G. Banwell, Matthew T. Jones, David T.J. Loong, David W. Lupton, David M. Pinkerton, Jayanta K. Ray, Anthony C. Willis

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

16 Citations (Scopus)

Abstract

The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.

Original language	English
Pages (from-to)	9252-9262
Number of pages	11
Journal	Tetrahedron
Volume	66
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2010.09.042
Publication status	Published - 20 Nov 2010

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title = "A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds",

abstract = "The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.",

keywords = "Cross-coupling, Oxindoles, Reductive cyclization, Ullmann reaction",

author = "Banwell, {Martin G.} and Jones, {Matthew T.} and Loong, {David T.J.} and Lupton, {David W.} and Pinkerton, {David M.} and Ray, {Jayanta K.} and Willis, {Anthony C.}",

year = "2010",

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doi = "10.1016/j.tet.2010.09.042",

language = "English",

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T1 - A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds

AU - Banwell, Martin G.

AU - Jones, Matthew T.

AU - Loong, David T.J.

AU - Lupton, David W.

AU - Pinkerton, David M.

AU - Ray, Jayanta K.

AU - Willis, Anthony C.

PY - 2010/11/20

Y1 - 2010/11/20

N2 - The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.

AB - The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.

KW - Cross-coupling

KW - Oxindoles

KW - Reductive cyclization

KW - Ullmann reaction

UR - http://www.scopus.com/inward/record.url?scp=78049269935&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2010.09.042

DO - 10.1016/j.tet.2010.09.042

M3 - Article

SN - 0040-4020

VL - 66

SP - 9252

EP - 9262

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds

Abstract

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