Ni- and Fe-Catalyzed Cross-Coupling Reactions of Phenol Derivatives
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
Org. Process Res. Dev., 2013, 17 (1), pp 29–39
DOI: 10.1021/op300236f
Publication Date (Web): December 11, 2012
Copyright © 2012 American Chemical Society
Abstract
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.
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Received 28 August 2012
Published online 11 December 2012
Published in print 18 January 2013
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Ni- and Fe-Catalyzed Cross-Coupling Reactions of Phenol Derivatives
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
Org. Process Res. Dev., 2013, 17 (1), pp 29–39
DOI: 10.1021/op300236f
Publication Date (Web): December 11, 2012
Copyright © 2012 American Chemical Society
Abstract
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.
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