Two-step synthesis of di- and tristannylarenes from anilines via an SRN1 mechanism

Gustavo F Silbestri,María T Lockhart,Alicia B Chopa,Panayiotis A Koutentis

doi:10.3998/ark.5550190.0012.718

Gustavo F Silbestri, María T Lockhart + Show 2 more

Open Access

https://doi.org/10.3998/ark.5550190.0012.718

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Abstract

The synthesis in good yields (71-85%) of di- and tristannylated benzenes from commercially available anilines, involving their conversion to the corresponding aryltrimethylammonium salts followed by the reaction with Me3SnNa 1 in liquid ammonia, is described. The results obtained clearly indicate that the stannylation reactions proceed through an SRN1 mechanism.

Highlights

The synthesis of organotin compounds and their application as intermediates has become a very important aspect in organic chemistry.[1]
We have synthesized mono, bi- and tristannylbenzenes by the reaction of different aryl diethyl phosphates with organostannides.7d we have demonstrated that monostannylarenes could be synthesized, in excellent yields, from anilines via the reaction of their trimethylammonium salts with organostannides, in liquid ammonia, by an SRN1 mechanism.7b It is important to note that this alternative route to the synthesis of organostannanes avoids the use of Grignard reagents or organolithium compounds
These results clearly indicate that the reaction goes through an SRN1 mechanism, as shown in Scheme 1, and that there is a spontaneous electron transfer (ET) which is stimulated under irradiation

Summary

Introduction

The synthesis of organotin compounds and their application as intermediates has become a very important aspect in organic chemistry.[1]. In this work we describe the results obtained from the reaction of a series of aryltrimethylammonium salts, supporting more than one leaving group, with Me3SnNa 1 in liquid ammonia.

Results

Conclusion