Journal Article Mechanistic Investigation of RhI-Catalyzed Cycloisomerization of Benzylallene-Internal Alkynes via C-H Activation

Kawaguchi, Yasuaki  ,  Yasuda, Shigeo  ,  Mukai, Chisato

82 ( 14 )  , pp.7666 - 7674 , 2017-07-21 , American Chemical Society
ISSN:0022-3263
NCID:AA12097242
Description
Treatment of the benzylallene-internal alkynes with [RhCl(CO)2]2 effected a cycloisomerization via a Csp2-H bond activation to produce the tricyclo[9.4.0.03,8]pentadecapentaene skeleton. The reaction mechanism via formation of the rhodabicyclo[4.3.0] intermediates and σ-bond metathesis between the Csp2-H bond on the benzene ring and the Csp2-RhIII bond was proposed. In addition, a plausible alternative mechanism for the previously reported cycloisomerization of the benzylallene-terminal alkynes could also be proposed. © 2017 American Chemical Society.
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