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 in | Angewandte Chemie International Edition Vol. 58; no. 32; pp. 10941 - 10945 |
|---|---|
| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
05.08.2019
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.201904707 |
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| Abstract | 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. |
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| AbstractList | 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 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. 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 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. |
| Author | Wang, Zhu‐Yin Luo, Yong‐Chun Yan, Lei Xu, Peng‐Fei Yu, Wan‐Lei Liu, Dan |
| Author_xml | – sequence: 1 givenname: Wan‐Lei surname: Yu fullname: Yu, Wan‐Lei organization: Lanzhou University – sequence: 2 givenname: Yong‐Chun surname: Luo fullname: Luo, Yong‐Chun organization: Lanzhou University – sequence: 3 givenname: Lei surname: Yan fullname: Yan, Lei organization: Lanzhou University – sequence: 4 givenname: Dan surname: Liu fullname: Liu, Dan organization: Lanzhou University – sequence: 5 givenname: Zhu‐Yin surname: Wang fullname: Wang, Zhu‐Yin organization: Lanzhou University – sequence: 6 givenname: Peng‐Fei orcidid: 0000-0002-5746-758X surname: Xu fullname: Xu, Peng‐Fei email: xupf@lzu.edu.cn organization: Lanzhou University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31166076$$D View this record in MEDLINE/PubMed |
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| Keywords | 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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| Snippet | A synergistic catalytic method combining photoredox catalysis, hydrogen‐atom transfer, and proton‐reduction catalysis for the dehydrogenative silylation of... A synergistic catalytic method combining photoredox catalysis, hydrogen-atom transfer, and proton-reduction catalysis for the dehydrogenative silylation of... |
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| SubjectTerms | 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 |
| Title | Dehydrogenative Silylation of Alkenes for the Synthesis of Substituted Allylsilanes by Photoredox, Hydrogen‐Atom Transfer, and Cobalt Catalysis |
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