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Iridium(I)-Catalyzed C‒C and C‒N Bond Formation Reactions via Borrowing Hydrogen Strategy.

08:00 EDT 15th April 2019 | BioPortfolio

Summary of "Iridium(I)-Catalyzed C‒C and C‒N Bond Formation Reactions via Borrowing Hydrogen Strategy."

Iridium(I) complexes having an imidazol-2-ylidene ligand with benzylic wingtips efficiently catalyzed the β-alkylation of secondary alcohols with primary alcohols and acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones through a borrowing hydrogen pathway. The β-alkylated alcohols, including cholesterol derivatives, and substituted quinolines were obtained in good yields by using a minute amount of catalyst with a catalytic amount of NaOH or KOH under air atmosphere liberating water (and H2 in the case of quinoline synthesis) as the sole-byproduct. Notably, this system demonstrated TONs of 940000 (for β-alkylation of secondary alcohols with primary alcohols by using down to 0.0001 mol% = 1 ppm of catalyst) and 9200 (acceptorless dehydrogenative cyclization of 2-aminobenzyl alcohol with ketones).

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This article was published in the following journal.

Name: The Journal of organic chemistry
ISSN: 1520-6904
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