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A reaction of [2,6-(tBu2PO)2C6H3]NiSCH2Ph with BH3·THF: borane mediated C–S bond cleavage

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Abstract

C–S bond activation of thiophenols and mercaptans is of great importance but has rarely been reported. In this paper we report the C–S bond cleavage of the thiolato ligand of [2,6-(tBu2PO)2C6H3]NiSCH2Ph (1) mediated by BH3·THF. The treatment of 1 with an excess amount of BH3·THF in THF at room temperature afforded the borohydride complex [2,6-(tBu2PO)2C6H3]Ni(η2-BH4) (2) as the only product. The reaction of 1 with 2 equiv. of BH3·THF in THF at room temperature for 48 h produced the hydride complex [2,6-(tBu2PO)2C6H3]NiH (3) and the mercapto complex [2,6-(tBu2PO)2C6H3]NiSH (5). As a new complex, 5 was also independently synthesized by a salt metathesis reaction of the corresponding chloride complex with NaSH and fully characterized by multinuclear NMR, FTIR, HRMS, X-ray crystallography and elemental analysis. A possible mechanism for the formation of 5 was proposed. It was supposed that 5 formed through BH3 mediated C–S bond cleavage of the thiolato ligand of 1. The result would initiate further studies on the transition metal catalyzed borane mediated C–S bond activation of mercaptans.

Graphical abstract: A reaction of [2,6-(tBu2PO)2C6H3]NiSCH2Ph with BH3·THF: borane mediated C–S bond cleavage

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Publication details

The article was received on 26 Dec 2017, accepted on 29 Jan 2018 and first published on 30 Jan 2018


Article type: Paper
DOI: 10.1039/C7DT04883A
Citation: Dalton Trans., 2018, Advance Article
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    A reaction of [2,6-(tBu2PO)2C6H3]NiSCH2Ph with BH3·THF: borane mediated C–S bond cleavage

    J. Zhang, T. Liu, Q. Ma, S. Li and X. Chen, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C7DT04883A

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