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A silicon‐assisted synthesis of ( E )‐β‐haloenamides from N ‐vinylamides
Author(s) -
SzudkowskaFrątczak Justyna,
Zaranek Maciej,
Hreczycho Grzegorz,
Kubicki Maciej,
Grabarkiewicz Tomasz,
Pawluć Piotr
Publication year - 2015
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3284
Subject(s) - chemistry , ruthenium , silylation , stereoselectivity , stereospecificity , silicon , decomposition , stereochemistry , iodine , sequence (biology) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry
( E )‐β‐Iodoenamides and ( E )‐β‐iodoenimides can be easily obtained from N ‐vinyl derivatives ( N ‐vinylamides and N ‐vinylimides) by stereoselective ruthenium‐catalysed silylative coupling with vinyltrimethylsilane (Marciniec coupling) and subsequent stereospecific silicon–iodine exchange. Bromodesilylation of ( E )‐β‐silylenimides affords ( E )‐β‐bromoenimides, while the analogous reactions involving ( E )‐β‐silylenamides lead to decomposition of substrates. N ‐Halosuccinimides have been found as the most effective halogenating agents in the desilylation step under mild conditions. The ruthenium‐catalysed silylation/halodesilylation sequence can be performed in a one‐pot procedure . Copyright © 2015 John Wiley & Sons, Ltd.