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Gold(I)‐Catalyzed Decarboxylation of Propargyl Carbonates: Reactivity Reversal of the Gold Catalyst from π ‐Lewis Acidity to σ ‐Lewis Acidity
Author(s) -
Shen Ruwei,
Yang Jianjun,
Zhu Shugao,
Chen Chao,
Wu Luling
Publication year - 2015
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.201401094
Subject(s) - chemistry , propargyl , lewis acids and bases , decarboxylation , catalysis , cationic polymerization , reactivity (psychology) , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
A cationic gold(I)‐catalyzed decarboxylative etherification of propargyl carbonates to selectively produce propargyl ethers is reported. In the reaction the gold(I) catalyst shows a distinct σ ‐Lewis acidity rather than the commonly observed π ‐Lewis acidity, and thus catalyzes the decarboxylation of a variety of propargyl carbonates to give the corresponding propargyl ethers with high selectivity. This reaction represents a rare example of the tunable reactivity of cationic gold(I) complexes between σ ‐Lewis acidity and π ‐Lewis acidity.