One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.
One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides.
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DOI：
10.1039/c6sc03924c
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发表时间：
2017-02-01
期刊：
影响因子：
8.4
通讯作者：
Willis MC
中科院分区：
文献类型：
--
作者：
Davies AT;Curto JM;Bagley SW;Willis MC
描述了利用钯催化从芳基溴和杂芳基溴温和、有效地合成磺酰氟。描述了利用钯催化从芳基溴和杂芳基溴温和、有效地合成磺酰氟。该工艺涉及使用 DABSO 作为 SO2 源对芳基溴化物进行初始钯催化磺酰化，然后用亲电子氟源 NFSI 对所得亚磺酸盐进行原位处理。该序列代表了芳基溴磺酰化的第一个通用方法，并为先前描述的磺酰氟合成提供了实用的一锅法替代方案，允许快速获得这些生物学上重要的分子。证明了优异的官能团耐受性，对许多活性药物成分及其前体成功实现了转化。还演示了肽衍生的磺酰氟的制备。
A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described. The process involves the initial palladium-catalyzed sulfonylation of aryl bromides using DABSO as an SO2 source, followed by in situ treatment of the resultant sulfinate with the electrophilic fluorine source NFSI. This sequence represents the first general method for the sulfonylation of aryl bromides, and offers a practical, one-pot alternative to previously described syntheses of sulfonyl fluorides, allowing rapid access to these biologically important molecules. Excellent functional group tolerance is demonstrated, with the transformation successfully achieved on a number of active pharmaceutical ingredients, and their precursors. The preparation of peptide-derived sulfonyl fluorides is also demonstrated.