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Broad Functionalization of Deep-Cavity Cavitands by Directed ortho Metalation

✍ Scribed by Kannupal Srinivasan; Zachary R. Laughrey; Bruce C. Gibb

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
302 KB
Volume
2008
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The endo‐ and exo‐rim positions of deep‐cavity cavitand 1 were functionalized by directed ortho metalation (D__o__M) procedures. A range of electrophilic quenchers led to hosts with ester, phenol and thioether functionality. In each case, a combination of host pre‐organization and reaction control resulted in far fewer products than the theoretical sixty‐nine. In addition to the nature of the lithiate, functionalization patterns were also dependent on the electrophile, with a general trend that the non‐carbon electrophiles examined gave higher degrees of substitution. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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