Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles.
Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles.
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DOI：
10.1039/c9ob02408e
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发表时间：
2019-12
影响因子：
3.2
通讯作者：
Julin Gong;Kun Hu;Yinlin Shao;Renhao Li;Yetong Zhang;Mao‐Lin Hu;Jiuxi Chen
中科院分区：
文献类型：
--
作者：
Julin Gong;Kun Hu;Yinlin Shao;Renhao Li;Yetong Zhang;Mao‐Lin Hu;Jiuxi Chen
首次报道了钯催化的2-（2-酰基苯氧基）乙腈与芳基硼酸的串联加成/环化反应，为2-芳酰基苯并呋喃的合成提供了一种新的策略，具有良好的化学选择性和广泛的官能团相容性。初步的机理实验表明，这一串联过程涉及顺序亲核加成生成2-（2-酰基苯氧基）-1-苯基乙-1-酮，然后分子内环化。该方法也被应用于合成2-芳酰基吲哚和有效的CYP 19抑制剂1-（苯并呋喃-2-基（苯基）甲基）-1H-1，2，4-三唑。
The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2-(2-acylphenoxy)-1-phenylethan-1-one followed by an intramolecular cyclization. This methodology has also been applied to the synthesis of 2-aroyl indoles and the potent CYP19 inhibitor 1-(benzofuran-2-yl(phenyl)methyl)-1H-1,2,4-triazole.