Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades,Chemical Science

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Synthesis of azasilacyclopentenes and silanols via Huisgen cycloaddition-initiated C–H bond insertion cascades
Chemical Science ( IF 7.6 ) Pub Date : 2017-09-04 00:00:00 , DOI: 10.1039/c7sc03130k
Jiun-Le Shih _{1,

2,

3,

4} , Santa Jansone-Popova _{1,

2,

3,

4} , Christopher Huynh _{1,

2,

3,

4} , Jeremy A. May _{1,

2,

3,

4}

Affiliation

An unusual transition metal-free cascade reaction of alkynyl carbonazidates was discovered to form azasilacyclopentenes. Mild thermolysis afforded the products via a series of cyclizations, rearrangements, and an α-silyl C–H bond insertion (rather than the more common Wolff rearrangement, 1,2-shift, or β-silyl C–H insertion) to form silacyclopropanes. A mechanistic proposal for the sequence was informed by control experiments and the characterization of reaction intermediates. The substrate scope and post-cascade transformations were also explored.

中文翻译：

通过Huisgen环加成引发的C–H键插入级联反应合成氮杂硅环戊烯和硅烷醇

发现碳氮炔基炔烃的一种不寻常的无过渡金属的级联反应，可形成氮杂硅环戊烯。温和的热分解通过一系列环化，重排和α-甲硅烷基C–H键插入（而不是更常见的Wolff重排，1,2-移位或β-甲硅烷基CH插入）形成硅环丙烷。通过控制实验和反应中间体的表征，为该顺序提供了一种机械方案。还探讨了底物范围和级联后转换。

更新日期：2017-09-25

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