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Multicomponent Mannich reactions through C-H bond activation is described. These transformations allowed the straightforward generation of densely substituted benzylic and homo-benzylic amines in good yields. The reaction involves a reaction between two transient species: an organometallic species, generated by transition metal-catalyzed sp2 or sp3 C-H bond activation and an in situ generated imine. The use of an acetal as an aldehyde surrogate was found essential for the reaction to proceed. The process could be successfully applied to Rh(III)-catalyzed sp2 C-H bond functionalization and extended to Cu(II)-catalyzed sp3 C-H bond functionalization.
This article was published in the following journal.
Name: Chemistry (Weinheim an der Bergstrasse, Germany)
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Ketonic amines prepared from the condensation of a ketone with formaldehyde and ammonia or a primary or secondary amine. A Mannich base can act as the equivalent of an alpha,beta unsaturated ketone in synthesis or can be reduced to form physiologically active amino alcohols.
Chemical bond cleavage reactions resulting from absorption of radiant energy.
A hepatic carcinogen whose mechanism of activation involves N-hydroxylation to the aryl hydroxamic acid followed by enzymatic sulfonation to sulfoxyfluorenylacetamide. It is used to study the carcinogenicity and mutagenicity of aromatic amines.
Derivatives of benzylic acid, including its salts and esters,
Enzymes of the isomerase class that catalyze reactions in which a group can be regarded as eliminated from one part of a molecule, leaving a double bond, while remaining covalently attached to the molecule. (From Enzyme Nomenclature, 1992) EC 5.5.