DIRECTED ORTHO-METALATION CROSS-COUPLING LINKS - CARBAMOYL RENDITION OF THE BAKER-VENKATARAMAN REARRANGEMENT - REGIOSPECIFIC ROUTE TO SUBSTITUTED 4-HYDROXYCOUMARINS

Authors
KALININ AV DASILVA AJM LOPES CC LOPES RSC SNIECKUS V
Citation
Av. Kalinin et al., DIRECTED ORTHO-METALATION CROSS-COUPLING LINKS - CARBAMOYL RENDITION OF THE BAKER-VENKATARAMAN REARRANGEMENT - REGIOSPECIFIC ROUTE TO SUBSTITUTED 4-HYDROXYCOUMARINS, Tetrahedron letters, 39(28), 1998, pp. 4995-4998
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
28
Year of publication
1998
Pages
4995 - 4998
Database
ISI
SICI code
0040-4039(1998)39:28<4995:DOCL-C>2.0.ZU;2-9
Abstract
A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a ge neral synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently pr epared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence prov ides a regiospecific anionic Friedel-Crafts complement for the constru ction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science L td. All rights reserved.