Iron-Catalyzed
Directed C(sp<sup>2</sup>)–H
and C(sp<sup>3</sup>)–H Functionalization with Trimethylaluminum
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Abstract
Conversion of a C(sp<sup>2</sup>)–H or C(sp<sup>3</sup>)–H
bond to the corresponding C–Me bond can be achieved by using
AlMe<sub>3</sub> 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
