Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides
Graphical abstract
Introduction
The use of oxidative gold catalysis as an effective means of facilitating C–C bond-forming reactions has been attracting increasing amount of attention in recent years [1]. The fact that Au (I) and Pd(0) are isoelectronics means that Au (I) species are able to catalyse reactions, including cross-coupling reactions, that are typically promoted by Pd(0). A number of Au(I) catalysts have therefore been successfully used in several of these reactions, such as Suzuki [2], Sonogashira [3], Stille [1](h), [4] and Hiyama [5] couplings.
The higher redox potential that exists between Au(I) and Au(III) could be seen as a drawback. However, the Au(I)/Au(III) redox cycle takes place quite easily in the presence of external oxidants [1](h), [2](f), [6].
A number of research group have recently presented a new strategy for gold-catalysed cross-coupling reactions [7]. They propose using aryl radicals, which operate as both oxidants and coupling partners, instead of external oxidants. These aryl radicals usually resulted from the light-mediated decomposition of arenediazoniumm salts after nitrogen loss, which generally occurred in the presence of an appropriate photocatalyst. Two efficient gold-catalysed Suzuki-Miyaura couplings of arenediazonium salts that make use of this mechanism have been recently reported [8], [8](a), [8](b). This approach was recently improved into a photocatalyst-free coupling as proposed by Hashmi and co-workers [8c].
Our own research has produced a large family of dry diazonium salts, the arenediazonium o-benzenedisulfonimides 1 (Fig. 1) [9a], which, have shown significant potential in numerous synthetic applications and in particular have given excellent results in palladium catalysed coupling reactions [[9], [9](b), [9](c), [9](d), [9](e), [9](f), [9](g), [9](h)].
In fact, they are easy to prepare and isolate, are extremely stable, and can be stored for an unlimited period. Moreover, they react easily both in water and in organic solvents, and o-benzenedisulfonimide (2; Fig. 1) can be easily recovered and reused at the end of the reactions.
As part of a broader project aimed at exploring the synthetic potential of 1 in metal catalysed reactions we herein describe the reactivity of 1 as electrophilic partners in Au(I) catalysed Suzuki-Miyaura coupling [10] (Scheme 1). It must be stressed that, in our recent paper [[11], [11](a)], we obtained significant results from using salts 1 in Au(I) catalysed Heck-coupling reactions.
Section snippets
Results and discussion
In order to optimise the reaction conditions, the coupling reaction of benzenediazonium o-benzenedisulfonimide (1a) and 4-methoxyphenylboronic acid (3a) in the presence of two different Au(I) catalysts was initially performed and studied under varying conditions, as reported in Table 1. First of all, it must be stressed that better results were achieved using [bis(trifluoromethanesulfonyl)imidate] (triphenylphosphine) gold (Table 1, entries 13–24) than with chloro(triphenylphosphine)gold (
Conclusions
We have proposed a mild, easy and efficient gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides 1 and heteroarenediazonium o-benzenedisulfonimides 5. The target products, biaryls 4 or heteroarenes 6 were generally obtained in satisfactory yields (51 positive examples, 80% average yield). We also confirm the interesting role that the o-benzenedisulfonimide anion plays as an electron transfer agent in enabling a pathway that does not require the presence of
General information
All the reactions were carried out in oven dried glassware and under a nitrogen flow. Analytical grade reagents and solvents were used and reactions were monitored by GC, GC-MS and TLC. Column chromatography and TLC were performed on Merck silica gel 60 (70–230 mesh ASTM) and GF 254, respectively. Petroleum ether refers to the fraction boiling in the range 40–70 °C. Room temperature is 20–25 °C. Mass spectra were recorded on an HP 5989B mass selective detector connected to an HP 5890 GC with a
Acknowledgements
This work has been supported by the University of Torino and the Ministero dell’Università e della Ricerca.
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