title: 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.
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Fumihiko
authors.initials: F
authors.lastname: Toriyama
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Josep
authors.initials: J
authors.lastname: Cornella
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Laurin
authors.initials: L
authors.lastname: Wimmer
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Tie-Gen
authors.initials: TG
authors.lastname: Chen
authors.affiliation: Chemical Development, Bristol-Myers Squibb , One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Darryl D
authors.initials: DD
authors.lastname: Dixon
authors.affiliation: Chemical Development, Bristol-Myers Squibb , One Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: Gardner
authors.initials: G
authors.lastname: Creech
authors.affiliation: Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors.forename: Phil S
authors.initials: PS
authors.lastname: Baran
mesh_terms: D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D007501:Iron / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction
chemical_list: D004952:Esters; D002244:Carbon; D007501:Iron