Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride,Chemical Science

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Palladium-catalyzed regiodivergent hydroaminocarbonylation of alkenes to primary amides with ammonium chloride
Chemical Science ( IF 7.6 ) Pub Date : 2017-10-24 00:00:00 , DOI: 10.1039/c7sc04054g
Bao Gao _{1,

2,

3,

4,

5} , Guoying Zhang _{1,

2,

3,

4,

5} , Xibing Zhou _{1,

2,

3,

4,

5} , Hanmin Huang _{1,

2,

3,

4,

5}

Affiliation

Palladium-catalyzed hydroaminocarbonylation of alkenes for the synthesis of primary amides has long been an elusive aim. Here, we report an efficient catalytic system which enables inexpensive NH₄Cl to be utilized as a practical alternative to gaseous ammonia for the palladium-catalyzed alkene-hydroaminocarbonylation reaction. Through appropriate choice of the palladium precursors and ligands, either branched or linear primary amides can be obtained in good yields with good to excellent regioselectivities. Primary mechanistic studies were conducted and disclosed that electrophilic acylpalladium species were capable of capturing the NH₂-moiety from ammonium salts to form amides in the presence of CO with NMP as a base.

中文翻译：

钯与氯化铵催化的烯烃区域发散性氢氨基羰基化为伯酰胺

钯催化烯烃的氢氨基羰基化反应以合成伯酰胺一直是一个遥不可及的目标。在这里，我们报告了一种有效的催化系统，该系统可使廉价的NH ₄ Cl用作钯催化的烯烃-氢氨基羰基化反应的气态氨的实用替代品。通过的钯前体和配体，或者支链或直链伯酰胺可以以良好产率与卓越的区域选择性地获得合适的选择。进行了初步的机理研究，并揭示了亲电子的酰基铝物种能够在NMP为碱的CO存在下，从铵盐中捕获NH _2-部分以形成酰胺。

更新日期：2017-11-07

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