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Nucleophile-Controlled Trapping of Gold Carbene by Nitriles and Water: Synthesis of 5H-Pyrimido[5,4-b]indoles and 2-Benzylidene-3-indolinones.

Yun-Long Zhu, Yi-Fan Dong, Si-Ru Wang,You-Gui Li,Xiang Wu,Long-Wu Ye

Organic letters(2024)

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摘要
A gold-catalyzed, nucleophile-controlled cascade reaction of N-(2-azidophenyl-ynyl)methanesulfonamides with nitriles and water is described that provides structurally diverse 5H-pyrimido[5,4-b]indoles and 2-benzylidene-3-indolinones in good to excellent yields. Mechanistic studies indicate that the beta- sulfonamido-alpha-imino gold carbene is the key intermediate which is generated through the gold-catalyzed cyclization of N-(2azidophenyl-ynyl)methanesulfonamides and undergoes formal [4 + 2] cascade annulation with nitriles and intramolecular S(N)2 ' type reaction with water, respectively.
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