Carbon-coated mesoporous silica incorporating organoruthenium complexes and its application to hydrosilylation of 1-hexy
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Carbon‑coated mesoporous silica incorporating organoruthenium complexes and its application to hydrosilylation of 1‑hexyne Dang Van Do1 · Takuya Hosokawa2 · Yu Horiuchi2 · Masaya Matsuoka2 Received: 13 April 2020 / Accepted: 31 August 2020 © Springer Nature B.V. 2020
Abstract The present article describes the construction of the organoruthenium complex catalyst within carbon-coated mesoporous silica and its application to a heterogeneous catalyst for hydrosilylation reaction. The carbon-coated mesoporous silica (C-MCM-41) was synthesized by carbonization of 2,3-dihydroxynaphthalene (DN) adsorbed on the surface of mesoporous silica, followed by the ligand exchange reaction between [(CH3CN)3RuCp]PF6 (Cp: cyclopentadienyl) and six-membered carbon ring at the surface of C-MCM-41 ([C-MCM-41-RuCp]PF6). X-ray absorption fine structure study for [C-MCM-41-RuCp]PF6 demonstrates that the structure of the constructed ruthenium complex is closely similar to that of a molecular [(C6H6) RuCp]PF6 complex. The [C-MCM-41-RuCp]PF6 behaves as a heterogeneous ruthenium complex catalyst and promotes hydrosilylation of 1-hexyne by triethylsilane in a solid–gas heterogeneous system to give α-vinylsilane as a major product. Keywords Carbon-coated mesoporous silica · Organoruthenium complex · Heterogeneous catalyst · Hydrosilylation
Introduction Vinylsilanes are important building blocks in various organic synthesis reactions, such as conjugate addition reaction and cross-coupling reaction [1–5]. Of the available methods for the preparation of vinylsilanes, hydrosilylation of alkynes * Yu Horiuchi [email protected]‑u.ac.jp * Masaya Matsuoka [email protected]‑u.ac.jp 1
Faculty of Chemistry, VNU University of Science, 19 Le Thanh Tong, Hoan Kiem , Ha Noi, Viet Nam
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Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1‑1 Gakuen‑Cho, Naka‑Ku, Sakai, Osaka 599‑8531, Japan
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is the most important [6–10]. A lot of catalysts were used for promoting hydrosilylation reactions, such as ruthenium complexes [11–16] and rhodium complexes [2, 17, 18]. Among those, [(CH3CN)3RuCp]PF6 is one of the most important complexes because of its high catalytic activity. Besides, this complex is well known to undergo ligand exchange in arene compounds to give the corresponding arene complexes [19–21] (Scheme 1). Taking advantage of this phenomenon, this type of Ru complexes has been constructed successfully within arene moieties in phenylene- and biphenylenebridged hybrid mesoporous material (denoted as HMM-ph and HMM-biph, respectively) by use of a simple ligand-exchange reaction with [(CH3CN)3RuCp] PF6 [22, 23]. The constructed organoruthenium complexes within HMMs consist of Ru center directly coordinated by arene moieties of HMMs as “framework ligand” and interestingly show efficient catalytic activity in the selective hydrosilylation of 1-hexyne in a solid–gas heterogeneous system at temperatures above 473 K. On the other hand, there has been intense interes
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