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Issue 3, 2021
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Nucleophilic reactivity of the gold atom in a diarylborylgold(i) complex toward polar multiple bonds

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Abstract

A di(o-tolyl)borylgold complex was synthesized via the metathesis reaction of a gold alkoxide with tetra(o-tolyl)diborane(4). The resulting diarylborylgold complex exhibited a Lewis acidic boron center and a characteristic visible absorption that arises from its HOMO–LUMO excitation, which is narrower than that of a previously reported dioxyborylgold complex. The diarylborylgold complex reacted with isocyanide in a stepwise fashion to afford single- and double-insertion products and a C–C coupled product. Reactions of this diarylborylgold complex with C[double bond, length as m-dash]O/N double bond species furnished addition products under concomitant formation of Au–C and B–O/N bonds, which suggests nucleophilic reactivity of the gold metal center. DFT calculations provided details of the underlying reaction mechanism, which involves an initial coordination of the C[double bond, length as m-dash]O/N bond to the boron vacant p-orbital of the diarylboryl ligand followed by a migration of the gold atom from the tetracoordinate sp3-hybridized boron center, which is analogous to the reactivity of the conventional sp3-hybridized borate species. The DFT calculations also suggested a stepwise mechanism for the reaction of this diarylborylgold complex with isocyanide, which afforded three different reaction products depending on the applied reaction conditions.

Graphical abstract: Nucleophilic reactivity of the gold atom in a diarylborylgold(i) complex toward polar multiple bonds

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Article information


Submitted
02 Oct 2020
Accepted
17 Nov 2020
First published
18 Nov 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 917-928
Article type
Edge Article

Nucleophilic reactivity of the gold atom in a diarylborylgold(I) complex toward polar multiple bonds

A. Suzuki, X. Guo, Z. Lin and M. Yamashita, Chem. Sci., 2021, 12, 917 DOI: 10.1039/D0SC05478J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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