Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen‐Atom Transfer, and Cobalt Catalysis

A synergistic catalytic method combining photoredox catalysis, hydrogen‐atom transfer, and proton‐reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditi...

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Published inAngewandte Chemie International Edition Vol. 58; no. 32; pp. 10941 - 10945
Main Authors Yu, Wan‐Lei, Luo, Yong‐Chun, Yan, Lei, Liu, Dan, Wang, Zhu‐Yin, Xu, Peng‐Fei
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 05.08.2019
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkenes
allylic compounds
Atom economy
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cobalt
Dehydrogenation
hydrogen atom transfer
Oxidants
Oxidizing agents
photochemistry
Photoredox catalysis
Physical Sciences
radicals
Reaction mechanisms
Science & Technology
Substitutes
ORGANIC-SYNTHESIS
ACTIVATION
radicals
ALKYLATION
HYDROSILYLATION
cobalt
hydrogen atom transfer
FUNCTIONALIZATION
ALCOHOLS
EVOLUTION
photochemistry
allylic compounds
OLEFINS
VISIBLE-LIGHT IRRADIATION
WATER
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Summary:A synergistic catalytic method combining photoredox catalysis, hydrogen‐atom transfer, and proton‐reduction catalysis for the dehydrogenative silylation of alkenes was developed. With this approach, a highly concise route to substituted allylsilanes has been achieved under very mild reaction conditions without using oxidants. This transformation features good to excellent yields, operational simplicity, and high atom economy. Based on control experiments, a possible reaction mechanism is proposed. A synergistic catalytic method of combining photoredox catalysis, hydrogen‐atom transfer, and proton‐reduction catalysis for the dehydrogenative silylation of alkenes was developed. The reaction features high regioselectivity, excellent tolerance of functional groups, wide substrate scope, and mild reaction conditions. Moreover, this oxidant‐free system offers a cleaner and more efficient method beyond traditional catalysis, which requires either stoichiometric or excess amounts of oxidants.
Bibliography:Medline
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.201904707