A novel mode of access to polyfunctional organotin compounds and their reactivity in Stille cross-coupling reaction

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Abstract

Mono-, di-, tri- and tetra-functional organotin compounds were easily prepared in a sonicated Barbier reaction using ultrasound technology via coupling reaction of organo halides with tin halides (Bu3SnCl, Bu2SnCl2, BuSnCl3, SnCl4) mediated by magnesium metal. The di- and tri-functional organotin compounds were tested in a Stille cross-coupling reaction in order to ascertain how many groups were transferred.

Graphical abstract

Mono-, di-, tri- and tetra-functional organotin compounds were easily prepared in a sonicated Barbier reaction using ultrasound technology via coupling reaction of organo halides with tin halides (Bu3SnCl, Bu2SnCl2, BuSnCl3, SnCl4) mediated by magnesium metal. The di- and tri-functional organotin compounds were tested in a Stille cross-coupling reaction in order to ascertain how many groups were transferred.

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Introduction

The considerable advances in the use of organotin compounds as reagents or intermediates in organic synthesis in recent years have prompted the preparation of many new organotin compounds and the development of new rapid and convenient synthesis procedures [1]. The formation of a carbon–carbon bond by organotin compounds (especially tributylstannyl compounds) and electrophiles is of considerable interest. Palladium-catalysed cross-coupling of organotin compounds with organic electrophiles (Stille reaction) has emerged as one of the main methods for the creation of new carbon–carbon bonds [2]. Organotin compounds have been extensively accessed in organic synthesis and are typically prepared by the reaction of organometallic compound (RMgX, Rli, RZnX, etc.) which will react with organotin halides (RnSnCl4−n) or by reactions of stannylanions with organic halides [3]. Alkynyltin compounds are typically prepared by condensation of 1-alkynes with R3SnNR′2 or R3SnOR′ and also by trapping of an alkynyl metal with R3SnX [4]. These methods allow synthesis of mono-, di-, tri- and tetra-functional organotin compounds, but in particular mono-functional tributylorganotin compounds have been synthesised with yields varying according to the nature of the substituent. We were therefore interested to synthesise various mono-, di-, tri- and tetra- functional organotin compounds by sonication in order to improve yields and the methodology and to create new organotin compounds according to our laboratory experience [5]. The increased focus on the use of sonochemical methods in organic synthesis has been demonstrated by the many reports in the literature on sonochemical reactions [6]. However few publications have reported the synthesis of mono-functional tributyltin compounds [7] and none have reported the synthesis of di-, tri- and tetra-functional organotin compounds with this technology.

Section snippets

Preparation of mono-, di-, tri- and tetra-functional organotin compounds

We first tested a simplified and improved one-step synthesis of organotin compounds by Barbier reaction between stannyl chlorides, magnesium turnings and organic halides using ultrasound, without the presence of dibromoethane or iodine, as previously recommended for the synthesis of only mono-functional organotin compounds [7] (Scheme 1).

A wide range of organotin compounds were subjected to this procedure to produce quite high yields of the corresponding products. A clean multi-substitution

Experimental

1H NMR spectra were recorded on a Bruker AC 200 (200 MHz) using CDCl3 as solvent. The results, reported using the residual proton resonance of CDCl3 (δH = 7.25 ppm) as the internal reference, were as follows (in order): chemical shift (d in ppm relative to Me4Si), multiplicity (s, d, t, m, b for singlet, doublet, triplet, multiplet, broad), coupling constants (J in Hz). 13C NMR spectra were recorded at 50.3 MHz on the same instrument using the CDCl3 solvent peak at δC = 77.0 ppm as reference. Mass

Acknowledgments

We thank the CNRS and MRT for providing financial support, and the “Service d’analyse chimique du Vivant de Tours” for recording NMR and mass spectra.

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