Gold(I)‐Catalyzed Decarboxylation of Propargyl Carbonates: Reactivity Reversal of the Gold Catalyst from  π ‐Lewis Acidity to  σ ‐Lewis Acidity | Zendy

Shen Ruwei | Zendy; Yang Jianjun | Zendy; Zhu Shugao | Zendy; Chen Chao | Zendy; Wu Luling | Zendy

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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.

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