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Ruthenium-catalyzed cascade C-H functionalization of phenylacetophenones.

ABSTRACT: Three orthogonal cascade CH functionalization processes are described, based on ruthenium-catalyzed CH alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl2 }2 ] and stoichiometric Cu(OAc)2 . Each transformation uses CH functionalization methods to form CC bonds sequentially, with the indeno furanone synthesis featuring a CO bond formation as the terminating step. This work demonstrates the power of ruthenium-catalyzed alkenylation as a platform reaction to develop more complex transformations, with multiple CH functionalization steps taking place in a single operation to access novel carbocyclic structures.

SUBMITTER: Mehta VP

PROVIDER: S-EPMC4265981 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Ruthenium-catalyzed cascade C-H functionalization of phenylacetophenones.

Mehta Vaibhav P VP García-López José-Antonio JA Greaney Michael F MF

Angewandte Chemie (International ed. in English) 20140122 6

Three orthogonal cascade CH functionalization processes are described, based on ruthenium-catalyzed CH alkenylation. 1-Indanones, indeno indenes, and indeno furanones were accessed through cascade pathways by using arylacetophenones as substrates under conditions of catalytic [{Ru(p-cymene)Cl2 }2 ] and stoichiometric Cu(OAc)2 . Each transformation uses CH functionalization methods to form CC bonds sequentially, with the indeno furanone synthesis featuring a CO bond formation as the terminat ...[more]

PMID: 24453063

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