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Synthesis 2010(21): 3715-3723  
DOI: 10.1055/s-0030-1258214
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Tris(pentafluorophenyl)borane-Catalyzed Alkylation of 1,3-Dicarbonyl Compounds with Benzylic Alcohols: Access to Oxygenated Heterocycles

Chada Raji Reddy*a, Jonnalagadda Vijaykumara, René Gréeb
a Organic Division - I, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160512; e-Mail: rajireddy@iict.res.in;
b Université de Rennes 1, Laboratoire CPM, CNRS UMR 6510 and Laboratoire SCR, CNRS UMR 6226, Avenue du Général Leclerc, 35042 Rennes Cedex, France
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Publikationsverlauf

Received 29 June 2010
Publikationsdatum:
13. August 2010 (online)

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Abstract

Tris(pentafluorophenyl)borane has found to be an effective catalyst for the alkylation of 1,3-dicarbonyl compounds using benzylic alcohols as alkylating agents. Various 1,3-dicarbonyl compounds reacted cleanly with different benzylic alcohols to provide the corresponding monoalkylated products in good yield. In addition tris(pentafluorophenyl)borane efficiently promoted the C3 alkylation of 4-hydroxycoumarins. Further, several oxygenated heterocycles such as furans, 4H-chromenes, and furanocoumarins have been prepared using the described methodology as the key step.

Key words

tris(pentafluorophenyl)borane - 1,3-dicarbonyl compound - benzylic alcohol - alkylation - heterocycle

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