Rhodium(I)‐Catalyzed Cycloisomerization of Benzylallene‐Alkynes through CH Activation | Zendy

Kawaguchi Yasuaki | Zendy; Yasuda Shigeo | Zendy; Kaneko Akira | Zendy; Oura Yuki | Zendy; Mukai Chisato | Zendy

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Rhodium(I)‐Catalyzed Cycloisomerization of Benzylallene‐Alkynes through CH Activation

Author(s) -

Kawaguchi Yasuaki,

Yasuda Shigeo,

Kaneko Akira,

Oura Yuki,

Mukai Chisato

Publication year - 2014

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201403990

Subject(s) - cycloisomerization , rhodium , chemistry , catalysis , medicinal chemistry , electrophile , stereochemistry , organic chemistry

The efficient Rh I ‐catalyzed cycloisomerization of benzylallene‐alkynes produced the tricyclo[9.4.0.0 3,8 ]pentadecapentaene skeleton through a C sp 2H bond activation in good yields. A plausible reaction mechanism proceeds via oxidative addition of the acetylenic CH bond to Rh I , an ene‐type cyclization to the vinylidenecarbene–Rh I intermediate, and an electrophilic aromatic substitution with the vinylidenecarbene species. It was proposed based on deuteration and competition experiments.

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