Alkene synthesis using phosphonium ylides as umpolung reagents

We report a transformation between a well‐known nucleophile, phosphonium ylide, and an electrophile. Subsequent ylide‐ylide coupling achieves unusual (Z )‐selectivity as compared to the conventional Wittig olefination. The synthesis of medium‐sized ring olefins has also been demonstrated, together w...

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Main Authors: Vu, Minh Duy, Leng, Wei-Lin, Hsu, Hao-Cheng, Liu, Xue-Wei
Other Authors: School of Physical and Mathematical Sciences
Format: Journal Article
Language:English
Published: 2020
Subjects:
Online Access:https://hdl.handle.net/10356/139819
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author Vu, Minh Duy
Leng, Wei-Lin
Hsu, Hao-Cheng
Liu, Xue-Wei
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Vu, Minh Duy
Leng, Wei-Lin
Hsu, Hao-Cheng
Liu, Xue-Wei
author_sort Vu, Minh Duy
collection NTU
description We report a transformation between a well‐known nucleophile, phosphonium ylide, and an electrophile. Subsequent ylide‐ylide coupling achieves unusual (Z )‐selectivity as compared to the conventional Wittig olefination. The synthesis of medium‐sized ring olefins has also been demonstrated, together with a one‐pot olefination from activated halides.
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spelling ntu-10356/1398192020-05-29T08:36:34Z Alkene synthesis using phosphonium ylides as umpolung reagents Vu, Minh Duy Leng, Wei-Lin Hsu, Hao-Cheng Liu, Xue-Wei School of Physical and Mathematical Sciences Science::Chemistry Ylides Photoredox Catalysis We report a transformation between a well‐known nucleophile, phosphonium ylide, and an electrophile. Subsequent ylide‐ylide coupling achieves unusual (Z )‐selectivity as compared to the conventional Wittig olefination. The synthesis of medium‐sized ring olefins has also been demonstrated, together with a one‐pot olefination from activated halides. NRF (Natl Research Foundation, S’pore) MOE (Min. of Education, S’pore) 2020-05-22T00:56:35Z 2020-05-22T00:56:35Z 2018 Journal Article Vu, M. D., Leng, W.-L., Hsu, H.-C., & Liu, X.-W. (2019). Alkene synthesis using phosphonium ylides as umpolung reagents. Asian Journal of Organic Chemistry, 8(1), 93-96. doi:10.1002/ajoc.201800586 2193-5807 https://hdl.handle.net/10356/139819 10.1002/ajoc.201800586 2-s2.0-85056660986 1 8 93 96 en Asian Journal of Organic Chemistry © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved.
spellingShingle Science::Chemistry
Ylides
Photoredox Catalysis
Vu, Minh Duy
Leng, Wei-Lin
Hsu, Hao-Cheng
Liu, Xue-Wei
Alkene synthesis using phosphonium ylides as umpolung reagents
title Alkene synthesis using phosphonium ylides as umpolung reagents
title_full Alkene synthesis using phosphonium ylides as umpolung reagents
title_fullStr Alkene synthesis using phosphonium ylides as umpolung reagents
title_full_unstemmed Alkene synthesis using phosphonium ylides as umpolung reagents
title_short Alkene synthesis using phosphonium ylides as umpolung reagents
title_sort alkene synthesis using phosphonium ylides as umpolung reagents
topic Science::Chemistry
Ylides
Photoredox Catalysis
url https://hdl.handle.net/10356/139819
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