Journal
TETRAHEDRON
Volume 69, Issue 21, Pages 4338-4352Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.03.016
Keywords
Arylboronate; Aryne; Regioselectivity; Diels-Alder reaction; Grignard reagent
Categories
Funding
- KAKENHI [19890182]
- MEXT
- Japan Society for the Promotion of Science
- Daicel Chemical Industry Award in Synthetic Organic Chemistry (Japan)
- Grants-in-Aid for Scientific Research [19890182, 25460157, 23790017, 11J10892, 25460018] Funding Source: KAKEN
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3-Borylbenzynes were generated in situ from 6-boryl-2-iodophenyl trifluoromethanesulfonates using i-PrMgCl center dot LiCl and applied to Diels-Alder reactions with substituted furans and pyrroles. The reactions allowed good functional group compatibility and produced the cycloadducts in high yields with high distal selectivities. Effective conversion of the boryl group of the products was achieved. A series of these reactions provides a new method for producing multifunctionalized benzo-fused aromatic compounds. Additionally, the regioselectivities of these Diels-Alder reactions were theoretically analyzed by DFT calculations to find that the reactions were mainly controlled by the electrostatic effect and aryne distortion caused by the boryl group. (C) 2013 Elsevier Ltd. All rights reserved.
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