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Catalytic Reductive Cleavage of Poly(phenylene sulfide) Using a HydrosilaneThis work was supported financially by the DIC Corporation and the National Institute of Advanced Industrial Science and Technology (AIST). Y.M. also acknowledges a Grant-in-Aid Scientific Research (C) (19K05481 to Y.M.) from the JSPS and the Fujimori foundation.
The solvent-insoluble poly(phenylene sulfide) main chain was reductively cleaved by using triethylsilane as a hydrogen source under palladium/IcHex catalytic conditions. After the reaction, benzene and bis(triethylsilyl) sulfide as a sulfide source were formed efficiently. This method could be operated on a gram scale.
Received: 30 April 2021
Accepted after revision: 27 May 2021
Accepted Manuscript online:
27 May 2021
Article published online:
06 July 2021
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14 According to Sigma-Aldrich, Inc, prices of triethylsilane, trimethoxysilane, triethoxysilane, and bis(trimethylsiloxy)methylsilane are 111 USD/mol (ordering scale, 500 g, 99%), 551 USD/mol (ordering scale, 100 g, 95%), 491 USD/mol (ordering scale, 50 mL, 95%), and 156 USD/mol (ordering scale, 250 mL, 97%).
15 See the Supporting Information.
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20 In addition, we attempted the reaction of di(4-bromophenyl) sulfide with triethylsilane under the present catalytic conditions to compare the reactivity between C–S and C–Br bonds. As a result, the C–Br bond was cleaved mainly. See the Supporting Information.
For, disilyl sulfides as a sulfur source, see: