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Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

ABSTRACT: A series of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with a mesylate leads to a new class of precatalysts with improved solution stability and that are readily prepared from a wider range of phosphine ligands. The differences between the previous version of precatalyst and that reported here are explored. In addition, the reactivity of the latter is examined in a range of C-C and C-N bond forming reactions.

SUBMITTER: Bruno NC

PROVIDER: S-EPMC3647481 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

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Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.

Bruno Nicholas C NC Tudge Matthew T MT Buchwald Stephen L SL

Chemical science 20130101

A series of easily prepared, phosphine-ligated palladium precatalysts based on the 2-aminobiphenyl scaffold have been prepared. The role of the precatalyst-associated labile halide (or pseudohalide) in the formation and stability of the palladacycle has been examined. It was found that replacing the chloride in the previous version of the precatalyst with a mesylate leads to a new class of precatalysts with improved solution stability and that are readily prepared from a wider range of phosphine ...[more]

PMID: 23667737

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