Ni- and Fe-Catalyzed Cross-Coupling Reactions of Phenol Derivatives

This review describes our laboratory’s efforts to develop transition metal-catalyzed cross-couplings of several unconventional phenol-based electrophiles. Specifically, we highlight herein the following four key transformations: (a) nickel-catalyzed Suzuki–Miyaura couplings of aryl pivalates, carbam...

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Veröffentlicht in:Organic process research & development 2013-01, Vol.17 (1), p.29-39
Hauptverfasser: Mesganaw, Tehetena, Garg, Neil K
Format: Artikel
Sprache:eng
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Zusammenfassung:This review describes our laboratory’s efforts to develop transition metal-catalyzed cross-couplings of several unconventional phenol-based electrophiles. Specifically, we highlight herein the following four key transformations: (a) nickel-catalyzed Suzuki–Miyaura couplings of aryl pivalates, carbamates, and sulfamates to construct sp2–sp2 C–C bonds; (b) iron-catalyzed Kumada couplings of aryl carbamates and sulfamates for the assembly of sp2–sp3 C–C bonds; (c) nickel-catalyzed amination reactions of carbamates and sulfamates to build aryl C–N bonds; and (d) nickel-catalyzed reductive cleavage reactions of aryl carbamates to achieve aryl deoxygenation and a rare method for cine substitution. We expect this review will enable the greater use of unconventional phenol-based cross-coupling electrophiles in industrial settings.
ISSN:1083-6160
1520-586X
DOI:10.1021/op300236f