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Palladium‐Catalyzed Oxidative Carbocyclization–Borylation of Enallenes to Cyclobutenes
Author(s) -
Qiu Youai,
Yang Bin,
Zhu Can,
Bäckvall JanE.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601613
Subject(s) - borylation , chemistry , palladium , imide , cyclobutene , catalysis , oxidative phosphorylation , substrate (aquarium) , combinatorial chemistry , alkene , alkyl , functional group , oxidative addition , organic chemistry , aryl , biochemistry , ring (chemistry) , oceanography , polymer , geology
A highly efficient palladium‐catalyzed oxidative borylation of enallenes was developed for the selective formation of cyclobutene derivatives and fully‐substituted alkenylboron compounds. Cyclobutenes are formed as the exclusive products in MeOH in the presence of H 2 O and Et 3 N, whereas the use of AcOH leads to alkenylboron compounds. Both reactions showed a broad substrate scope and good tolerance for various functional groups, including carboxylic acid ester, free hydroxy, imide, and alkyl groups. Furthermore, transformations of the borylated products were conducted to show their potential applications.