Premium
Broad Functionalization of Deep‐Cavity Cavitands by Directed ortho Metalation (Eur. J. Org. Chem. 19/2008)
Author(s) -
Srinivasan Kannupal,
Laughrey Zachary R.,
Gibb Bruce C.
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200890048
Subject(s) - metalation , surface modification , chemistry , electrophile , combinatorial chemistry , stereochemistry , nanotechnology , organic chemistry , materials science , catalysis
Abstract The cover picture shows a collection of china, pewter cups, mugs, and jugs. For these and other macroscale objects, it is easier to decorate their exterior rather than their interior surface. Not surprisingly, the same asymmetry is seen at the molecular scale; it is generally easier to decorate/functionalize a convex than a concave surface. One approach to endo functionalization of deep‐cavity cavitands is directed ortho metalation (D o M). In the paper by Srinivasan et al., on p. 3265 ff, it is shown that various electrophiles quench the lithiates formed according to D o M protocols. Reaction control leads to between one and five functional groups being introduced at the endo and exo positions of these hosts.