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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 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.201601613
Subject(s) - borylation , chemistry , cyclobutene , palladium , imide , catalysis , oxidative phosphorylation , alkene , substrate (aquarium) , alkyl , functional group , combinatorial chemistry , oxidative addition , organic chemistry , aryl , ring (chemistry) , biochemistry , 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.