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Synfacts 2011(10): 1111-1111
DOI: 10.1055/s-0030-1261076
DOI: 10.1055/s-0030-1261076
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Direct Suzuki-Miyaura Coupling of Phenol Derivatives via Mutual Activation
Contributor(s):Paul Knochel, Nadja M. BarlD.-G. Yu, Z.-J. Shi*
Peking University, Beijing and Shanghai Institute of Organic Chemistry, P. R. of China
Mutual Activation: Suzuki-Miayura Coupling through Direct Cleavage of the sp² C-O Bond of Naphtholate
Angew. Chem. Int. Ed. 2011, 50: 7097-7100
Peking University, Beijing and Shanghai Institute of Organic Chemistry, P. R. of China
Mutual Activation: Suzuki-Miayura Coupling through Direct Cleavage of the sp² C-O Bond of Naphtholate
Angew. Chem. Int. Ed. 2011, 50: 7097-7100
Further Information
Publication History
Publication Date:
20 September 2011 (online)
Key words
nickel - Suzuki coupling - C-O activation - phenols
Significance
Herein, a direct Ni-catalyzed Suzuki coupling of in situ generated sodium phenolates with aryl boroxines is reported. Key step is the formation of an aryl borate which simultaneously activates the two coupling partners.
Comment
Traditional preactivation of phenols and boronic acids is not necessary since the in situ generated borate mutually activates both the aryl C-O and the aryl C-B bonds. Nevertheless, it is shown that lack of the Lewis acid BEt3 as additional activator leads to decreased product yields.