One-pot synthesis of an indole-substituted 7, 8-dicarba-nido-dodecahydroundecaborate(−1). Issue 4 (3rd December 2014)

• Record Type: Journal Article
• Authors: Neumann, W.; Frank, R.; Hey-Hawkins, E.
• Is Part Of: Dalton transactions. Volume 44:Issue 4(2015)
• Page Start: 1748
• Page End: 1753
• Publication Date: 2014-12-03
• Subjects: Chemistry, Inorganic -- Periodicals; Chemistry, Physical and theoretical -- Periodicals; Chemistry, Inorganic -- Periodicals; 546.05
• DOI: 10.1039/c4dt03218g
• Languages: English
• ISSNs: 1477-9226

Abstract

Abstract : The generally difficult conjugation of two relevant pharmacophores, indole and carbaborane, has been readily achieved by sequential deboronation and substitution yielding a water-soluble carbaboranyl indole. Abstract : Carbaboranes are increasingly used as pharmacophores to replace phenyl substituents in established drug molecules. In contrast to traditional organic chemistry, elaborate procedures to introduce functionality frequently fail in the case of carbaboranes and their chemistry is often hampered by degradation of the cluster. Herein, the development of a one-pot synthesis of a water-soluble N-nido -dicarbaborato indole is presented, including a proposed mechanism for the reaction sequence. These studies provide useful synthetic tools for the conjugation of two important pharmacophores, indoles and carbaboranes.