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<p>In an effort to gain atom-economy, a one-pot sequential reaction has been demonstrated which begins with the in situ generation of allylstannane from allyl bromide, tin(II) halide, and catalytic palladium(0). In second step of the sequence allylstannane is reacted with an aldehyde or an imine to provide homoallyloxytin(IV) and homoallylazatin(IV), respectively. Finally in the third step, intermediate homoallyloxytin(IV) is coupled with an aldehyde, an arylepoxide, or an arene to afford different tetrahydropyrans, benzyl tetrahydropyrans, and 4,4-diarylbut-1-enes, respectively. On the other hand, reaction of water with homoallyloxytin(IV) or homoallylazatin(IV) led to the facile formation of corresponding homoallyl alcohols or homoallyl amines, respectively.</p> Graphical abstract <p></p>

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Enhancing the atom economy in allylstannane utilization: one-pot sequential nucleophilic and electrophilic activation

  • 期刊论文

  • 发表日期：

    2025年8月18日

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  • Ujjal Kanti Roy,
  • Partha Pratim Hajra

摘要

In an effort to gain atom-economy, a one-pot sequential reaction has been demonstrated which begins with the in situ generation of allylstannane from allyl bromide, tin(II) halide, and catalytic palladium(0). In second step of the sequence allylstannane is reacted with an aldehyde or an imine to provide homoallyloxytin(IV) and homoallylazatin(IV), respectively. Finally in the third step, intermediate homoallyloxytin(IV) is coupled with an aldehyde, an arylepoxide, or an arene to afford different tetrahydropyrans, benzyl tetrahydropyrans, and 4,4-diarylbut-1-enes, respectively. On the other hand, reaction of water with homoallyloxytin(IV) or homoallylazatin(IV) led to the facile formation of corresponding homoallyl alcohols or homoallyl amines, respectively.

Graphical abstract