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The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline

The addition of benzophenone to a FeCl(3)/CH(2)Cl(2) mixture in the presence of 3',4'-dimethoxy-2-acetamidostilbene 17 unexpectedly leads to a dramatic improvement in yield of the indoline 20 from 38% (previously reported by us) to 75.4%, after careful examination of a variety of reaction...

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Main Authors: Ariffin, Azhar, Hadi, A.H.A., Thomas, N.F., Kee, C.H., Awang, Khalijah, Weber, J.F.F., Lim, C.G., Mukhtar, M.R.
Format: Article
Published: 2008
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/8070/
http://www.heterocycles.jp/newlibrary/libraries/abst/02546
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spelling my.um.eprints.80702019-03-01T09:05:53Z http://eprints.um.edu.my/8070/ The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline Ariffin, Azhar Hadi, A.H.A. Thomas, N.F. Kee, C.H. Awang, Khalijah Weber, J.F.F. Lim, C.G. Mukhtar, M.R. QD Chemistry The addition of benzophenone to a FeCl(3)/CH(2)Cl(2) mixture in the presence of 3',4'-dimethoxy-2-acetamidostilbene 17 unexpectedly leads to a dramatic improvement in yield of the indoline 20 from 38% (previously reported by us) to 75.4%, after careful examination of a variety of reaction conditions. A catalytic cycle has been proposed that involves not only stilbene radical cations but also Fe(2+) promoted benzophenone ketyl radical formation which enhances cyclisation, suppresses dimerization and accounts for the virtually quantitative recovery of the benzophenone. 2008-01-22 Article PeerReviewed Ariffin, Azhar and Hadi, A.H.A. and Thomas, N.F. and Kee, C.H. and Awang, Khalijah and Weber, J.F.F. and Lim, C.G. and Mukhtar, M.R. (2008) The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline. Heterocycles, 75 (5). pp. 1097-1108. ISSN 0385-5414 http://www.heterocycles.jp/newlibrary/libraries/abst/02546
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic QD Chemistry
spellingShingle QD Chemistry
Ariffin, Azhar
Hadi, A.H.A.
Thomas, N.F.
Kee, C.H.
Awang, Khalijah
Weber, J.F.F.
Lim, C.G.
Mukhtar, M.R.
The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline
description The addition of benzophenone to a FeCl(3)/CH(2)Cl(2) mixture in the presence of 3',4'-dimethoxy-2-acetamidostilbene 17 unexpectedly leads to a dramatic improvement in yield of the indoline 20 from 38% (previously reported by us) to 75.4%, after careful examination of a variety of reaction conditions. A catalytic cycle has been proposed that involves not only stilbene radical cations but also Fe(2+) promoted benzophenone ketyl radical formation which enhances cyclisation, suppresses dimerization and accounts for the virtually quantitative recovery of the benzophenone.
format Article
author Ariffin, Azhar
Hadi, A.H.A.
Thomas, N.F.
Kee, C.H.
Awang, Khalijah
Weber, J.F.F.
Lim, C.G.
Mukhtar, M.R.
author_facet Ariffin, Azhar
Hadi, A.H.A.
Thomas, N.F.
Kee, C.H.
Awang, Khalijah
Weber, J.F.F.
Lim, C.G.
Mukhtar, M.R.
author_sort Ariffin, Azhar
title The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline
title_short The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline
title_full The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline
title_fullStr The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline
title_full_unstemmed The subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-Dimethoxyphenyl) indoline
title_sort subtle co-catalytic intervention of benzophenone in radical cation mediated cyclization - an improved synthesis of 2-(3 ',4 '-dimethoxyphenyl) indoline
publishDate 2008
url http://eprints.um.edu.my/8070/
http://www.heterocycles.jp/newlibrary/libraries/abst/02546
_version_ 1643688210046386176
score 13.214268

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