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Redox-Active Esters in Fe-Catalyzed C-C Coupling.

ABSTRACT: Cross-couplings of alkyl halides and organometallic species based on single electron transfer using Ni and Fe catalyst systems have been studied extensively, and separately, for decades. Here we demonstrate the first couplings of redox-active esters (both isolated and derived in situ from carboxylic acids) with organozinc and organomagnesium species using an Fe-based catalyst system originally developed for alkyl halides. This work is placed in context by showing a direct comparison with a Ni catalyst for >40 examples spanning a range of primary, secondary, and tertiary substrates. This new C-C coupling is scalable and sustainable, and it exhibits a number of clear advantages in several cases over its Ni-based counterpart.

SUBMITTER: Toriyama F

PROVIDER: S-EPMC5016806 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

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Redox-Active Esters in Fe-Catalyzed C-C Coupling.

Toriyama Fumihiko F Cornella Josep J Wimmer Laurin L Chen Tie-Gen TG Dixon Darryl D DD Creech Gardner G Baran Phil S PS

Journal of the American Chemical Society 20160829 35

Cross-couplings of alkyl halides and organometallic species based on single electron transfer using Ni and Fe catalyst systems have been studied extensively, and separately, for decades. Here we demonstrate the first couplings of redox-active esters (both isolated and derived in situ from carboxylic acids) with organozinc and organomagnesium species using an Fe-based catalyst system originally developed for alkyl halides. This work is placed in context by showing a direct comparison with a Ni ca ...[more]

PMID: 27548696

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