Synthesis 2011(10): 1537-1540  
DOI: 10.1055/s-0030-1260007
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Et2MeN×HI-Catalyzed Reaction of Arylboronic Acids with 2-Acyl-2,3-dihydro-4H-pyrans Leading to 2-Aryltetrahydrocyclopenta[1,3,2]dioxaboroles

Takahide Fukuyama*, Takahiro Okamura, Ilhyong Ryu
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan
Fax: +81(72)2549695; e-Mail: fukuyama@c.s.osakafu-u.ac.jp;
Further Information

Publication History

Received 8 October 2010
Publication Date:
15 April 2011 (online)

Abstract

The reaction of arylboronic acids with 2-acyl-2,3-dihydro-4H-pyrans proceeded smoothly in the presence of a catalytic amount of Et2MeN˙HI to give acyl-substituted 2-aryltetrahydrocyclopenta[1,3,2]dioxaboroles in good yields. The reaction is likely to involve the acid-catalyzed ring-opening reaction of pyrans, an intramolecular aldol reaction, and condensation with boronic acids.

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