Dedicated to the memory of Professor Keith Fagnou (1971–2009)
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Full Paper
2-Substituted Benzo[b]furans from (E)-1,2-Dichlorovinyl Ethers and Organoboron Reagents: Scope and Mechanistic Investigations into the One-Pot Suzuki Coupling/Direct Arylation†
Article first published online: 28 JUL 2010
DOI: 10.1002/ejoc.201000787
Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Geary, L. M. and Hultin, P. G. (2010), 2-Substituted Benzo[b]furans from (E)-1,2-Dichlorovinyl Ethers and Organoboron Reagents: Scope and Mechanistic Investigations into the One-Pot Suzuki Coupling/Direct Arylation. Eur. J. Org. Chem., 2010: 5563–5573. doi: 10.1002/ejoc.201000787
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Publication History
- Issue published online: 28 JUL 2010
- Article first published online: 28 JUL 2010
- Manuscript Received: 1 JUN 2010
Funded by
- Natural Sciences and Engineering Research Council of Canada
- NSERC
Keywords:
- Oxygen heterocycles;
- C-H activation;
- Cross-coupling;
- Palladium
Abstract
2-Substituted benzo[b]furans can easily be assembled from simple phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid synthesis of many analogues using essentially the same chemistry, of particular value in drug development. Results of kinetic isotope effect studies and investigations into the regioselectivity of the process indicate that the direct arylation step most likely does not involve an electrophilic palladation. The most likely mechanism lies somewhere on the continuum between a C–H bond metathesis and an assisted palladation or concerted metallation-deprotonation pathway.