Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: a gas- and reductant-free process.
Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: a gas- and reductant-free process.
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DOI：
10.1002/anie.201404527
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发表时间：
2014-09-15
影响因子：
16.6
通讯作者：
Willis, Michael C.
中科院分区：
文献类型：
--
作者：
Emmett, Edward J.;Hayter, Barry R.;Willis, Michael C.
磺酰基衍生的官能团存在于广泛的有用分子和材料中，尽管有各种可用的制备方法，但使用催化方法引入最基本的磺酰基构建块二氧化硫的工艺很少见。本文描述了一种简单的反应体系，该体系由二氧化硫替代物DABSO、三乙胺和钯(0)催化剂组成，用于将广泛的芳基和杂芳基卤化物有效地转化为相应的亚硫酸铵。这种无气体和无还原剂的反应的主要特点包括可以使用的钯(1 %)和配体(1.5 %)的低负载量，以及使用异丙醇作为溶剂和正式还原剂。亚硫酸铵产物被原位转化为各种含磺酰基的官能团，包括磺酸、磺酰氯和磺胺。
Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas- and reductant-free reaction include the low loadings of palladium (1 mol %) and ligand (1.5 mol %) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.
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影响因子：
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作者：
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通讯作者：
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