Rh(III)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes,Chemical Science

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Rh(III)-catalyzed tandem annulative redox-neutral arylation/amidation of aromatic tethered alkenes
Chemical Science ( IF 7.6 ) Pub Date : 2020-10-16 , DOI: 10.1039/d0sc04007j
Chao Chen _{1,

2,

3,

4,

5} , Chen Shi _{1,

2,

3,

4,

5} , Yaxi Yang _{1,

2,

3,

4,

5} , Bing Zhou _{1,

2,

3,

4,

5}

Affiliation

Transition-metal-catalyzed directed C–H functionalization has emerged as a powerful and straightforward tool to construct C–C bonds and C–N bonds. Among these processes, the intramolecular annulative alkene hydroarylation reaction has received much attention because this intramolecular annulation can produce more complex and high value-added structural motifs found in numerous natural products and bioactive molecules. Despite remarkable progress, these annulative protocols developed to date remain limited to hydroarylation and functionalization of one side of alkenes, thus largely limiting the structural diversity and complexity. Herein, we developed a rhodium(III)-catalyzed tandem annulative arylation/amidation reaction of aromatic tethered alkenes to deliver a variety of 2,3-dihydro-3-benzofuranmethanamine derivatives bearing an all-carbon quaternary stereo center by employing 3-substituted 1,4,2-dioxazol-5-ones as an amidating reagent to capture the transient C(sp³)–Rh intermediate. Notably, by simply changing the directing group, a second, unsymmetrical ortho C–H amidation/annulation can be achieved to provide tricyclic dihydrofuro[3,2-f]quinazolinones in good yields.

中文翻译：

Rh（III）催化的串联式环氧化还原中性芳族链烯的芳基化/酰胺化反应

过渡金属催化的定向C–H功能化已成为构建C–C键和C–N键的强大而直接的工具。在这些方法中，分子内环烯烃的氢芳基化反应受到了广泛的关注，因为这种分子内环化可以产生在许多天然产物和生物活性分子中发现的更复杂和高附加值的结构基序。尽管取得了显着进展，但迄今为止开发的这些环空方案仍仅限于烯烃一侧的氢芳基化和官能化，因此在很大程度上限制了结构的多样性和复杂性。在这里，我们开发了铑（III）催化的芳香族系链烯烃的串联环化芳基化/酰胺化反应，通过使用3-取代的1,4,2-二恶唑-5生成各种带有全碳四元立体中心的2,3-二氢-3-苯并呋喃甲胺衍生物-作为酰胺化试剂，用于捕获瞬态C（sp ³）-Rh中间体。值得注意的是，只需简单地改变导向基团，就可以实现第二次不对称的邻位C H酰胺化/环化反应，从而以高收率提供三环二氢呋喃并[3,2- f ]喹唑啉酮。

更新日期：2020-10-17

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