Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates

A new protocol for the anti-Markovnikov hydrofunctionalization of alkenyl alcohol O-Bn ethers was developed using xanthates as functionalizing agents in the presence of lauroyl peroxide as a radical initiator and a stoichiometric oxidant. The benzyl group serves as a traceless hydrogen donor in the...

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Main Authors:	Hayashi, Hirohito, Kaga, Atsushi, Wang, Bin, Gagosz, Fabien, Chiba, Shunsuke
Other Authors:	School of Physical and Mathematical Sciences
Format:	Article
Language:	English
Published:	2022
Subjects:	Science::Chemistry Alkene Derivative Benzyl Derivative
Online Access:	https://hdl.handle.net/10356/154849
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Institution:	Nanyang Technological University
Language:	English

id	sg-ntu-dr.10356-154849
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spelling	sg-ntu-dr.10356-1548492023-02-28T19:58:55Z Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates Hayashi, Hirohito Kaga, Atsushi Wang, Bin Gagosz, Fabien Chiba, Shunsuke School of Physical and Mathematical Sciences Science::Chemistry Alkene Derivative Benzyl Derivative A new protocol for the anti-Markovnikov hydrofunctionalization of alkenyl alcohol O-Bn ethers was developed using xanthates as functionalizing agents in the presence of lauroyl peroxide as a radical initiator and a stoichiometric oxidant. The benzyl group serves as a traceless hydrogen donor in the remote radical hydrogen atom transfer event during the process. Ministry of Education (MOE) Nanyang Technological University Accepted version This work was supported by funding from Nanyang Technological University (for S. C.), the Singapore Ministry of Education (Academic Research Fund Tier 1: RG2/15 for S. C.) and the Natural Sciences and Engineering Research Council (for F. G.). F. G. and S. C. are grateful to the PHC Merlion grant (Project 5.02.15) for the support of this collaboration project. 2022-01-14T08:27:50Z 2022-01-14T08:27:50Z 2018 Journal Article Hayashi, H., Kaga, A., Wang, B., Gagosz, F. & Chiba, S. (2018). Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates. Chemical Communications, 54(54), 7535-7538. https://dx.doi.org/10.1039/c8cc02971g 1359-7345 https://hdl.handle.net/10356/154849 10.1039/c8cc02971g 29926014 2-s2.0-85049515374 54 54 7535 7538 en RG2/15 Chemical Communications © 2018 The Royal Society of Chemistry. All rights reserved. This paper was published in Chemical Communications and is made available with permission of The Royal Society of Chemistry. 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 Derivative Benzyl Derivative
spellingShingle	Science::Chemistry Alkene Derivative Benzyl Derivative Hayashi, Hirohito Kaga, Atsushi Wang, Bin Gagosz, Fabien Chiba, Shunsuke Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates
description	A new protocol for the anti-Markovnikov hydrofunctionalization of alkenyl alcohol O-Bn ethers was developed using xanthates as functionalizing agents in the presence of lauroyl peroxide as a radical initiator and a stoichiometric oxidant. The benzyl group serves as a traceless hydrogen donor in the remote radical hydrogen atom transfer event during the process.
author2	School of Physical and Mathematical Sciences
author_facet	School of Physical and Mathematical Sciences Hayashi, Hirohito Kaga, Atsushi Wang, Bin Gagosz, Fabien Chiba, Shunsuke
format	Article
author	Hayashi, Hirohito Kaga, Atsushi Wang, Bin Gagosz, Fabien Chiba, Shunsuke
author_sort	Hayashi, Hirohito
title	Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates
title_short	Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates
title_full	Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates
title_fullStr	Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates
title_full_unstemmed	Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates
title_sort	use of a benzyl ether as a traceless hydrogen donor in the anti-markovnikov hydrofunctionalization of alkenes with xanthates
publishDate	2022
url	https://hdl.handle.net/10356/154849
_version_	1759854330027966464

Use of a benzyl ether as a traceless hydrogen donor in the anti-Markovnikov hydrofunctionalization of alkenes with xanthates

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