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Chemistry: A European Journal | 2016

Nickel-Catalyzed C−H Chalcogenation of Anilines

Thomas Müller; Lutz Ackermann

The C-H thiolation of aniline derivatives was accomplished with a versatile nickel(II) catalyst under ligand-free conditions. The robust nature of the nickel catalysis system was reflected by the C-H thiolation with a good functional group tolerance and an ample scope, employing anilines possessing removable directing groups. The widely applicable nickel catalyst also allowed for aniline C-H selenylations, while mechanistic studies provided strong support that the rate-determining step is the C-H activation.


Angewandte Chemie | 2018

1,4‐Iron Migration for Expedient Allene Annulations through Iron‐Catalyzed C−H/N−H/C−O/C−H Functionalizations

Jiayu Mo; Thomas Müller; João C. A. Oliveira; Lutz Ackermann

C-H activation bears great potential for enabling sustainable molecular syntheses in a step- and atom-economical manner, with major advances having been realized with precious 4d and 5d transition metals. In contrast, we employed earth abundant, nontoxic iron catalysts for versatile allene annulations through a unique C-H/N-H/C-O/C-H functionalization sequence. The powerful iron catalysis occurred under external-oxidant-free conditions even at room temperature, while detailed mechanistic studies revealed an unprecedented 1,4-iron migration regime for facile C-H activations.


Angewandte Chemie | 2017

Bifurcated Nickel-Catalyzed Functionalizations: Heteroarene C−H Activation with Allenes

Sachiyo Nakanowatari; Thomas Müller; João C. A. Oliveira; Lutz Ackermann

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