Palladium-catalyzed intermolecular heck-type reaction of epoxides

The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides,...

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التفاصيل البيبلوغرافية
المؤلفون الرئيسيون: Teng, Shenghan, Tessensohn, Malcolm Eugene, Webster, Richard David, Zhou, Steve Jianrong
مؤلفون آخرون: School of Physical and Mathematical Sciences
التنسيق: مقال
اللغة:English
منشور في: 2020
الموضوعات:
الوصول للمادة أونلاين:https://hdl.handle.net/10356/140177
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spelling sg-ntu-dr.10356-1401772020-05-27T04:25:23Z Palladium-catalyzed intermolecular heck-type reaction of epoxides Teng, Shenghan Tessensohn, Malcolm Eugene Webster, Richard David Zhou, Steve Jianrong School of Physical and Mathematical Sciences Science::Chemistry Heck Reaction Palladium Catalysis The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer. MOE (Min. of Education, S’pore) 2020-05-27T04:25:23Z 2020-05-27T04:25:23Z 2018 Journal Article Teng, S., Tessensohn, M. E., Webster, R. D., & Zhou, S. J. (2018). Palladium-catalyzed intermolecular heck-type reaction of epoxides. ACS Catalysis, 8(8), 7439-7444. doi:10.1021/acscatal.8b02029 2155-5435 https://hdl.handle.net/10356/140177 10.1021/acscatal.8b02029 2-s2.0-85049640355 8 8 7439 7444 en ACS Catalysis © 2018 American Chemical Society. All rights reserved.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic Science::Chemistry
Heck Reaction
Palladium Catalysis
spellingShingle Science::Chemistry
Heck Reaction
Palladium Catalysis
Teng, Shenghan
Tessensohn, Malcolm Eugene
Webster, Richard David
Zhou, Steve Jianrong
Palladium-catalyzed intermolecular heck-type reaction of epoxides
description The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Teng, Shenghan
Tessensohn, Malcolm Eugene
Webster, Richard David
Zhou, Steve Jianrong
format Article
author Teng, Shenghan
Tessensohn, Malcolm Eugene
Webster, Richard David
Zhou, Steve Jianrong
author_sort Teng, Shenghan
title Palladium-catalyzed intermolecular heck-type reaction of epoxides
title_short Palladium-catalyzed intermolecular heck-type reaction of epoxides
title_full Palladium-catalyzed intermolecular heck-type reaction of epoxides
title_fullStr Palladium-catalyzed intermolecular heck-type reaction of epoxides
title_full_unstemmed Palladium-catalyzed intermolecular heck-type reaction of epoxides
title_sort palladium-catalyzed intermolecular heck-type reaction of epoxides
publishDate 2020
url https://hdl.handle.net/10356/140177
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