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Regio‐ and Stereoselective Synthesis of Tri‐ and Tetrasubstituted Enamides via Palladium‐Catalyzed Silaboration of Ynamides
Author(s) -
Saito Nozomi,
Saito Keiichi,
Sato Hiroyasu,
Sato Yoshihiro
Publication year - 2013
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.201201111
Subject(s) - chemistry , regioselectivity , stereoselectivity , palladium , alkene , yield (engineering) , aryl , catalysis , combinatorial chemistry , silylation , coupling (piping) , stereochemistry , organic chemistry , mechanical engineering , materials science , alkyl , engineering , metallurgy
The palladium‐catalyzed silaboration of ynamides is demonstrated. The silaboration proceeds in a highly regioselective manner to give the corresponding tri‐ and tetrasubstituted enamide derivatives having both a silyl group and a boryl group on the alkene. Furthermore, the silaborated enamide could be utilized as a coupling partner in Suzuki–Miyaura coupling with aryl iodides to give the corresponding cross‐coupling product in good yield.