Premium
Palladium‐Catalyzed Cross‐Coupling Reaction of 1‐Aryltriazenes with Aryl‐ and Alkenyltrifluorosilanes
Author(s) -
Saeki Tomoyuki,
Matsunaga Tadafumi,
Son EunCheol,
Tamao Kohei
Publication year - 2004
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.200404212
Subject(s) - chemistry , palladium , lewis acids and bases , aryl , moiety , triazene , boron trifluoride , catalysis , coupling reaction , yield (engineering) , medicinal chemistry , organic chemistry , polymer chemistry , alkyl , materials science , metallurgy
The palladium‐catalyzed cross‐coupling reaction of 1‐aryltriazenes with aryl‐ and alkenyltrifluorosilanes occurs readily at room temperature to yield the corresponding biaryl and stilbene products in moderate to good yields. In contrast to the previous results for the reaction with areneboronic acids, in which an additional Lewis acid such as boron trifluoride is essential for the activation of the 1‐aryltriazenes, the Lewis acidity of organotrifluorosilanes seems to be strong enough to directly activate the triazene moiety to enter into the palladium‐catalyzed cross‐coupling reaction without an extra Lewis acid.