Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions
Abstract Here, the evolution of the titanocene‐catalyzed hydrosilylation of epoxides that yields the corresponding anti‐Markovnikov alcohols is summarized. The study focuses on aspects of sustainability, efficient catalyst activation, and stereoselectivity. The latest variant of the reaction employs...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Wiley
2023-07-01
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| Series: | Global Challenges |
| Subjects: | |
| Online Access: | https://doi.org/10.1002/gch2.202200240 |
| _version_ | 1797774870750167040 |
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| author | Sebastian Höthker Andreas Gansäuer |
| author_facet | Sebastian Höthker Andreas Gansäuer |
| author_sort | Sebastian Höthker |
| collection | DOAJ |
| description | Abstract Here, the evolution of the titanocene‐catalyzed hydrosilylation of epoxides that yields the corresponding anti‐Markovnikov alcohols is summarized. The study focuses on aspects of sustainability, efficient catalyst activation, and stereoselectivity. The latest variant of the reaction employs polymethylhydrosiloxane (PMHS), a waste product of the Müller–Rochow process as terminal reductant, features an efficient catalyst activation with benzylMgBr and the use of the bench stable Cp2TiCl2 as precatalyst. The combination of olefin epoxidation and epoxide hydrosilylation provides a uniquely efficient approach to the formal anti‐Markovnikov addition of H2O to olefins. |
| first_indexed | 2024-03-12T22:26:28Z |
| format | Article |
| id | doaj.art-33a40fe7c354497b8b3847c2174a9d5f |
| institution | Directory Open Access Journal |
| issn | 2056-6646 |
| language | English |
| last_indexed | 2024-03-12T22:26:28Z |
| publishDate | 2023-07-01 |
| publisher | Wiley |
| record_format | Article |
| series | Global Challenges |
| spelling | doaj.art-33a40fe7c354497b8b3847c2174a9d5f2023-07-22T04:24:12ZengWileyGlobal Challenges2056-66462023-07-0177n/an/a10.1002/gch2.202200240Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic ReactionsSebastian Höthker0Andreas Gansäuer1Kekulé‐Institut für Organische Chemie und Biochemie Rheinische Friedrich‐Wilhelms‐Universität Bonn Gerhard‐Domagk‐Straße 1 53121 Bonn GermanyKekulé‐Institut für Organische Chemie und Biochemie Rheinische Friedrich‐Wilhelms‐Universität Bonn Gerhard‐Domagk‐Straße 1 53121 Bonn GermanyAbstract Here, the evolution of the titanocene‐catalyzed hydrosilylation of epoxides that yields the corresponding anti‐Markovnikov alcohols is summarized. The study focuses on aspects of sustainability, efficient catalyst activation, and stereoselectivity. The latest variant of the reaction employs polymethylhydrosiloxane (PMHS), a waste product of the Müller–Rochow process as terminal reductant, features an efficient catalyst activation with benzylMgBr and the use of the bench stable Cp2TiCl2 as precatalyst. The combination of olefin epoxidation and epoxide hydrosilylation provides a uniquely efficient approach to the formal anti‐Markovnikov addition of H2O to olefins.https://doi.org/10.1002/gch2.202200240catalysisepoxidesgreen chemistryhydrosilylationsustainabilitytitanium |
| spellingShingle | Sebastian Höthker Andreas Gansäuer Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions Global Challenges catalysis epoxides green chemistry hydrosilylation sustainability titanium |
| title | Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions |
| title_full | Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions |
| title_fullStr | Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions |
| title_full_unstemmed | Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions |
| title_short | Formal Anti‐Markovnikov Addition of Water to Olefins by Titanocene‐Catalyzed Epoxide Hydrosilylation: From Stoichiometric to Sustainable Catalytic Reactions |
| title_sort | formal anti markovnikov addition of water to olefins by titanocene catalyzed epoxide hydrosilylation from stoichiometric to sustainable catalytic reactions |
| topic | catalysis epoxides green chemistry hydrosilylation sustainability titanium |
| url | https://doi.org/10.1002/gch2.202200240 |
| work_keys_str_mv | AT sebastianhothker formalantimarkovnikovadditionofwatertoolefinsbytitanocenecatalyzedepoxidehydrosilylationfromstoichiometrictosustainablecatalyticreactions AT andreasgansauer formalantimarkovnikovadditionofwatertoolefinsbytitanocenecatalyzedepoxidehydrosilylationfromstoichiometrictosustainablecatalyticreactions |