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Gold(I)‐Catalyzed Synthesis of Six‐Membered P,O‐Heterocycles via Hydration/Intramolecular Cyclization Cascade Reaction
Author(s) -
Zhang Shan,
Cheng Haiyang,
Mo Sheng,
Yin Shiwei,
Zhang Zunting,
Wang Tao
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900605
Subject(s) - chemoselectivity , chemistry , intramolecular force , alkyne , cascade , catalysis , cascade reaction , density functional theory , combinatorial chemistry , medicinal chemistry , stereochemistry , computational chemistry , organic chemistry , chromatography
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.