Site‐Selective C–C Cleavage of Benzocyclobutenones Enabled by a Blocking Strategy Using Nickel Catalysis

Controlling the chemo‐ and regioselectivity of transition‐metal‐catalyzed C−C activation remains a great challenge. The transformations of benzocyclobutenones (BCBs) usually involve the cleavage of C1−C2 bond. In this work, an unprecedented highly selective cleavage of C1−C8 bond with the insertion...

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Bibliographic Details
Published in:Angewandte Chemie 2021-08, Vol.133 (35), p.19227-19232
Main Authors: Guo, Jing‐Hong, Liu, Yu, Lin, Xin‐Cheng, Tang, Tian‐Mu, Wang, Bi‐Qin, Hu, Ping, Zhao, Ke‐Qing, Song, Feijie, Shi, Zhang‐Jie
Format: Article
Language:English
Subjects:
Alkynes
benzocyclobutenones
blocking strategy
Catalysis
Chemistry
Cleavage
C–C cleavage
Nickel
nickel catalysis
Regioselectivity
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Summary:Controlling the chemo‐ and regioselectivity of transition‐metal‐catalyzed C−C activation remains a great challenge. The transformations of benzocyclobutenones (BCBs) usually involve the cleavage of C1−C2 bond. In this work, an unprecedented highly selective cleavage of C1−C8 bond with the insertion of alkynes is achieved by using blocking strategy via Ni catalysis, providing an efficient method for synthesis of 1,8‐disubstituted naphthalenes. Notably, the blocking group could be readily removed after the transformation. A Ni‐catalyzed highly selective C1−C8 bond cleavage of BCBs with the insertion of alkynes was achieved by the assistance of a removable blocking group. This method provided an atom‐ and step‐economical approach to structurally important 1,8‐naphthalenediols under pH‐neutral conditions.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202106709