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Gold‐Catalyzed Synthesis of α‐Fluoro Acetals and α‐Fluoro Ketones from Alkynes
Author(s) -
de Haro Teresa,
Nevado Cristina
Publication year - 2010
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.201000559
Subject(s) - chemistry , selectfluor , regioselectivity , catalysis , alkyne , reaction conditions , organic chemistry , combinatorial chemistry , medicinal chemistry
A new method to synthesize α‐fluoro acetals and α‐fluoro ketones is presented here. In the presence of alcohols and Selectfluor, catalytic amounts of gold selectively transformed alkynes into the corresponding fluorinated acetals or ketones depending on the reaction conditions. This protocol has been applied to both terminal and internal alkynes showing a high degree of chemo‐ and regioselectivity. The reaction mechanism seems to proceed via two co‐existing pathways, since at least partially, the formation of the C( sp 3 )F bond in the final products occurs at the metal center.