Document Type

Article

Publication Date

9-2013

Publication Source

Heteroatom Chemistry

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

Volume

24

Issue

5

Peer Reviewed

yes