Cobalt(II)-catalyzed regio- And stereoselective hydroarylation of alkynes with organoboronic acids
The series of cobalt (II)-catalyzed cross-coupling reactions of organoboronic acids with alkynes was investigated. The reaction provided a convenient method for the synthesis of highly substituted olefins by using less expensive cobalt complexes as catalysts under base-free conditioned. The scope of organoboronic acids 1 and alkynes 2 in the addition reaction under the standard reaction conditions was also analyzed. Based on the known metal-catalyzed couplings of organometallic reagents and alkynes, a possible reaction mechanism for the present hydroarylation reaction was proposed. These are the first cobalt-catalyzed addition reactions of organoboronic acids to alkynes. The unusual trans stereochemistry for the hydroarylation of substituted propargyl alcohol and amine was observed. The results showed that the organoboronic acid plays a dual role, acting both as a carbon nucleophile as well as proton source in the reaction.
Cu-catalyzed stereoselective conjugate addition of arylboronic acids to alkynoates
The CuOAc-catalyzed reaction of internal alkynoates with arylboronic acids proceeded under mild conditions to yield trisubstituted cinnamates stereoselectively. The Royal Society of Chemistry.
Yamamoto, Yoshihiko,Kirai, Naohiro,Harada, Yu
supporting information; body text
p. 2010 - 2012
(2009/02/04)
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