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Article
Structure, Theoretical Studies and Coupling Reactions of Some New Cyclic Boronic Esters
Heteroatom Chemistry
  • Andrew Kuttler, University of Dayton
  • Sravanthi Durganala, University of Dayton
  • Albert Fratini, University of Dayton
  • Alexander Morgan, University of Dayton
  • Vladimir Benin, University of Dayton
Document Type
Article
Publication Date
9-1-2013
Abstract
The present report describes the X-ray structural and theoretical studies of some new pinacolboronate esters, and it also outlines the use of the target structures in Suzuki coupling reactions to produce new aromatic or heteroaromatic esters and amides. X-ray structural analysis of the studied compounds revealed that the pinacolborane ring's position with respect to the benzene ring varies, depending on the particular environment. An ortho-positioned carboxylic ester (methyl ester) causes a nearly perpendicular orientation of the pinacolborane unit with respect to the benzene ring, whereas an ortho-positioned amide (N,N-dimethylamide) causes the pinacolborane unit to orient itself nearly coplanar. A plausible explanation has been provided, based on both steric and electronic factors.
Inclusive pages
361-371
ISBN/ISSN
1042-7163
Document Version
Postprint
Comments

The document available for download is the authors' accepted manuscript, posted here in compliance with the publisher's policy on self-archiving. Some differences may exist between this version and the publisher's version; as such, researchers wishing to quote directly from it are advised to consult the version of record.

Permission documentation is on file.

Publisher
John Wiley & Sons
Peer Reviewed
Yes
Citation Information
Andrew Kuttler, Sravanthi Durganala, Albert Fratini, Alexander Morgan, et al.. "Structure, Theoretical Studies and Coupling Reactions of Some New Cyclic Boronic Esters" Heteroatom Chemistry Vol. 24 Iss. 5 (2013)
Available at: http://works.bepress.com/vladimir_benin/1/