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Carbogallation of Alkynes Using Gallium Tribromide and Silyl Ketene Acetals and Synthetic Application to Cross‐Coupling with Aryl Iodides
Author(s) -
Nishimoto Yoshihiro,
Ueda Hiroki,
Yasuda Makoto,
Baba Akio
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102255
Subject(s) - ketene , silylation , aryl , stereoselectivity , usability , chemistry , computer science , combinatorial chemistry , organic chemistry , catalysis , operating system , alkyl
Try substituted alkynes with GaBr 3 : The regio‐ and stereoselective carbogallation of alkynes has been achieved by a simple treatment of GaBr 3 , alkynes, and ketene silyl acetals. The produced alkenylgallium compounds can be used for the synthesis of selective trisubstituted alkenes through successive cross‐coupling with aryliodides (see scheme). The usability of the carbogallation was presented by the total synthesis of meroterpenoid nodosol, which was extracted from the seagrass Cymodocea nodosa.