3,4-DISUBSTITUTED FURANS .5. REGIOSPECIFIC MONO-IPSO-IODINATION OF 3,4-BIS(TRIMETHYLSILYL)FURAN AND REGIOSPECIFIC IPSO-IODINATION OF TRIS[(4-ALKYL OR 4-ARYL)FURAN-3-YL]BOROXINES TO 4-SUBSTITUTED 3-(TRIMETHYLSILYL)FURANS AND UNSYMMETRICAL 3,4-DISUBSTITUTED FURANS
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Abstract4-Iodo-3-trimethylsilylfuran (2), obtained through the regiospecific iodination of 3,4-bis(trimethylsilyl)furan (1), underwent either palladium- or nickel-catalyzed cross-coupling reactions with terminal alkenes, terminal alkynes, areneboronic acids, bis(p-methoxycarbonylbenzyl)zinc and Grignard reagents to give 4-substituted 3-(trimethylsilyl)furans 3-7, which were converted into boroxines 8. Regiospecific iodination of 8 gave iodofurans 9, which afforded in the usual way unsymmetrical 3,4-disubstituted furans 10. Boroxines 8 gave also 3,4-disubstituted furans 11 via palladium-catalyzed cross-coupling reactions with piperonyl chloride and vinyl bromide.
All Author(s) ListSONG ZZ, WONG HNC
Journal nameLIEBIGS ANNALEN DER CHEMIE
Year1994
Month1
Day1
Issue Number1
PublisherVCH PUBLISHERS INC
Pages29 - 34
ISSN0170-2041
LanguagesEnglish-United Kingdom
KeywordsBOROXINES; CROSS-COUPLING REACTION; FURANS; IODINATION, IPSO-
Web of Science Subject CategoriesChemistry; Chemistry, Multidisciplinary

Last updated on 2020-26-01 at 01:45