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Custom Hydrosilane Synthesis Based on Monosilane

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Presentation on theme: "Custom Hydrosilane Synthesis Based on Monosilane"— Presentation transcript:

1 Custom Hydrosilane Synthesis Based on Monosilane
Weiming Yuan, Polina Smirnov, Martin Oestreich  Chem  Volume 4, Issue 6, Pages (June 2018) DOI: /j.chempr Copyright © 2018 Elsevier Inc. Terms and Conditions

2 Chem 2018 4, DOI: ( /j.chempr ) Copyright © 2018 Elsevier Inc. Terms and Conditions

3 Figure 1 Silicon–Carbon Bond Formation and Hydrosilane Synthesis
(A) Traditional approach involving nucleophilic-substitution operations at the silicon atom. (B) Planned on-demand synthesis based on SiH4 surrogates revolving around a single central platform. Chem 2018 4, DOI: ( /j.chempr ) Copyright © 2018 Elsevier Inc. Terms and Conditions

4 Figure 2 Palladium-Catalyzed Arylation of SiH4 Surrogate 2 Followed by B(C6F5)3-Catalyzed Deprotection to Arrive at Trihydrosilanes Chem 2018 4, DOI: ( /j.chempr ) Copyright © 2018 Elsevier Inc. Terms and Conditions

5 Figure 3 Selective B(C6F5)3-Catalyzed Transfer Hydrosilylation Using Aryl-Substituted Surrogates 4c and 4j (A) Preparation of dihydrosilanes (left; 4 [0.3 mmol], 7 [0.1 mmol], B(C6F5)3 [0.01 mmol], CH2Cl2 [0.5 M], room temperature, 20 hr) and monohydrosilanes (right; 4 [0.10 mmol], 7 or 10 [0.21 mmol], B(C6F5)3 [0.010 mmol], CH2Cl2 [0.5 M], room temperature, 20 hr). (B) Preparation of silanes (4c [0.10 mmol], 7j or 7k [0.35 mmol], B(C6F5)3 [0.010 mmol], CH2Cl2 [0.5 M], room temperature, 20 hr). Chem 2018 4, DOI: ( /j.chempr ) Copyright © 2018 Elsevier Inc. Terms and Conditions

6 Figure 4 Further Diversification of the Aryl-Substituted Surrogate
(A) Stepwise installation of two different alkyl groups by platinum-catalyzed hydrosilylation followed by B(C6F5)3-catalyzed transfer hydrosilylation. (B) B(C6F5)3-catalyzed C–H silylation by electrophilic aromatic substitution combined with deprotection. Chem 2018 4, DOI: ( /j.chempr ) Copyright © 2018 Elsevier Inc. Terms and Conditions

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