Gold(I)‐Catalyzed Synthesis of Six‐Membered P, O‐Heterocycles via Hydration/Intramolecular Cyclization Cascade Reaction. Issue 18 (5th August 2019)

• Record Type: Journal Article
• Authors: Zhang, Shan; Cheng, Haiyang; Mo, Sheng; Yin, Shiwei; Zhang, Zunting; Wang, Tao
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 18(2019)
• Page Start: 4227
• Page End: 4231
• Publication Date: 2019-08-05
• Subjects: Gold-catalysis -- P, O-Heterocycles -- Chemoselectivity switch -- Cyclization -- DFT calculation; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900605
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Herein, we report the synthesis of six‐membered P, O‐heterocycles from dialkynylphosphine oxides. By using gold(I) complexes, the chemoselectivity of the reaction was switched from literature‐reported double hydration to a hydration/intramolecular cyclization cascade. Control experiments indicated that the first alkyne hydration product is an intermediate of the reaction. In addition, a density functional theory (DFT) calculation allowed to rationalize the observed chemoselectivity. Abstract :