Issue 6, 2000

A practical approach to stereodefined cyclopropyl-substituted heteroarenes using a Suzuki-type reaction

Abstract

In the presence of Pd(PPh3)4, NaBr and KF·2H2O the cross-coupling reaction of heteroaryl triflates with trans-cyclopropylboronic acids proceeds readily to give pure trans-cyclopropyl heteroarenes in moderate to good yields. The X-ray crystallography of compound 3g and 1H-NMR spectra of all products show that the configuration of the cyclopropyl group was retained during the reaction. Under the same reaction conditions, highly optically active cyclopropyl-substituted heteroarenes (up to 94% ee) were obtained by cross-coupling of heteroary/triflates with enantiomerically enriched cyclopropylboronic acids.

Supplementary files

Article information

Article type
Paper
Submitted
07 Feb 2000
Accepted
29 Mar 2000
First published
02 Jun 2000

New J. Chem., 2000,24, 425-428

A practical approach to stereodefined cyclopropyl-substituted heteroarenes using a Suzuki-type reaction

M. Yao and M. Deng, New J. Chem., 2000, 24, 425 DOI: 10.1039/B001051K

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