Iron-Catalyzed Directed C(sp2)-H and C(sp3)-H Functionalization with Trimethylaluminum
Conversion of a C(sp2)-H or C(sp3)-H bond to the corresponding C-Me bond can be achieved by using AlMe3 or its air-stable diamine complex in the presence of catalytic amounts of an inorganic iron(III) salt and a diphosphine along with 2,3-dichlorobutane as a stoichiometric oxidant. The reaction is applicable to a variety of amide substrates bearing a picolinoyl or 8-aminoquinolyl directing group, enabling methylation of a variety of (hetero)aryl, alkenyl, and alkyl amides. The use of the mild aluminum reagent prevents undesired reduction of iron and allows the reaction to proceed with catalyst turnover numbers as high as 6500.
Isoindolone synthesis via palladium-catalysed intramolecular amination of benzylic C-H bonds
A new method for the construction of isoindolones is presented in this paper. Four 7-methyl-2-(8-quinolinyl)-2,3-dihydro-1Hisoindol-1-ones were synthesised from 2,6-dimethyl -N-(8-quinolinyl)benzamides via intramolecular direct amination of benzylic C-H bonds. This approach provides a convenient method affording structurally new isoindolones for medicinal chemistry research.
Zhang, Ming
p. 606 - 610
(2013/11/06)
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