Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor

Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor

A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3 - or N3 -containing hypervalent iodine reagents, a series of homoallylic alcohol derivat...

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Main Authors: Lonca, Geoffroy Hervé, Ong, Derek Yiren, Tran, Thi Mai Huong, Tejo, Ciputra, Chiba, Shunsuke, Gagosz, Fabien
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Alkene Functionalization
Azidation
Online Access:https://hdl.handle.net/10356/154855
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1548552023-02-28T19:59:00Z Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor Lonca, Geoffroy Hervé Ong, Derek Yiren Tran, Thi Mai Huong Tejo, Ciputra Chiba, Shunsuke Gagosz, Fabien School of Physical and Mathematical Sciences Science::Chemistry Alkene Functionalization Azidation A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3 - or N3 -containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols. Ministry of Education (MOE) Nanyang Technological University Accepted version This research was supported by funding from Ecole Polytechnique (for F.G.), Nanyang Technological University (for S.C.), and the Singapore Ministry of Education (Academic Research Fund Tier 1: RG2/15 for S.C.). F.G. and S.C. are grateful for a PHC Merlion grant (Project 5.02.15) in support of this collaborative project. 2022-01-17T01:02:29Z 2022-01-17T01:02:29Z 2017 Journal Article Lonca, G. H., Ong, D. Y., Tran, T. M. H., Tejo, C., Chiba, S. & Gagosz, F. (2017). Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor. Angewandte Chemie International Edition, 129(38), 11598-11602. https://dx.doi.org/10.1002/anie.201705368 1433-7851 https://hdl.handle.net/10356/154855 10.1002/anie.201705368 28722345 2-s2.0-85028835877 38 129 11598 11602 en RG2/15 Angewandte Chemie International Edition This is the peer reviewed version of the following article: Lonca, G. H., Ong, D. Y., Tran, T. M. H., Tejo, C., Chiba, S. & Gagosz, F. (2017). Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor. Angewandte Chemie International Edition, 129(38), 11598-11602, which has been published in final form at https://doi.org/10.1002/ange.201705368. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Alkene Functionalization
Azidation
spellingShingle Science::Chemistry
Alkene Functionalization
Azidation
Lonca, Geoffroy Hervé
Ong, Derek Yiren
Tran, Thi Mai Huong
Tejo, Ciputra
Chiba, Shunsuke
Gagosz, Fabien
Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
description A protocol for the anti-Markovnikov hydrofunctionalization of alkenes has been developed by the use of a benzyl group as a traceless redox-active hydrogen donor. Under copper catalysis and in the presence of CF3 - or N3 -containing hypervalent iodine reagents, a series of homoallylic alcohol derivatives were hydrofunctionalized regioselectivity. A similar principle was also applied to the hydrofunctionalization of alkenols.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Lonca, Geoffroy Hervé
Ong, Derek Yiren
Tran, Thi Mai Huong
Tejo, Ciputra
Chiba, Shunsuke
Gagosz, Fabien
format Article
author Lonca, Geoffroy Hervé
Ong, Derek Yiren
Tran, Thi Mai Huong
Tejo, Ciputra
Chiba, Shunsuke
Gagosz, Fabien
author_sort Lonca, Geoffroy Hervé
title Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
title_short Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
title_full Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
title_fullStr Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
title_full_unstemmed Anti-Markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
title_sort anti-markovnikov hydrofunctionalization of alkenes : use of a benzyl group as a traceless redox-active hydrogen donor
publishDate 2022
url https://hdl.handle.net/10356/154855
_version_ 1759857180814606336

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