Palladium-Catalyzed C-S Bond Formation of Stable Enamines with Arene/Alkanethiols: Highly Regioselective Synthesis of β-Amino Sulfides

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• 作者：Yaojia Jiang ; Gaohui Liang ; Cong Zhang and Teck-Peng Loh
• 刊名：European Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 2016
• 年：2016
• 卷：2016
• 期：20
• 页码：3326-3330
• 全文大小：929K
• ISSN：1099-0690

文摘

A direct and regiocontrolled thiolation method to access β-amino sulfides through the palladium-catalyzed C(sp²)–H functionalization of stable enamines was described. The reaction was realized under mild conditions by adding an external phosphine ligand to prevent poisoning of the palladium catalyst by the sulfuric reagents. A possible mechanism was proposed according to the obtained results. The DFT calculation results were consistent with the experiment data, which gave the E isomers of the β-amino sulfides. The reaction was also performed on a gram scale and shows potential application in organic synthesis.