Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst

Siddhartha Das, Christopher D. Incarvito, Robert H. Crabtree, Gary W Brudvig

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301 Citations (Scopus)

Abstract

Although enzymes often incorporate molecular recognition elements to orient substrates selectively, such strategies are rarely achieved by synthetic catalysts. We combined molecular recognition through hydrogen bonding with C-H activation to obtain high-turnover catalytic regioselective functionalization of sp3 C-H bonds remote from the -COOH recognition group. The catalyst contains a Mn(μ-O)2Mn reactive center and a ligand based on Kemp's triacid that directs a -COOH group to anchor the carboxylic acid group of the substrate and thus modify the usual selectivity for oxidation. Control experiments supported the role of hydrogen bonding in orienting the substrate to achieve high selectivity.

Original languageEnglish
Pages (from-to)1941-1943
Number of pages3
JournalScience
Volume312
Issue number5782
DOIs
Publication statusPublished - Jun 30 2006

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Hydrogen Bonding
Carboxylic Acids
Ligands
Enzymes

ASJC Scopus subject areas

  • General

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Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst. / Das, Siddhartha; Incarvito, Christopher D.; Crabtree, Robert H.; Brudvig, Gary W.

In: Science, Vol. 312, No. 5782, 30.06.2006, p. 1941-1943.

Research output: Contribution to journalArticle

Das, Siddhartha ; Incarvito, Christopher D. ; Crabtree, Robert H. ; Brudvig, Gary W. / Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst. In: Science. 2006 ; Vol. 312, No. 5782. pp. 1941-1943.
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