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Synthesis of o ‐Allyloxy(ethynyl)benzene Derivatives by Cu‐Catalyzed Suzuki–Miyaura‐Type Reaction and Their Transformations into Heterocyclic Compounds
Author(s) -
Watanabe Kohei,
Mino Takashi,
Ishikawa Eri,
Okano Miyu,
Ikematsu Tatsuya,
Yoshida Yasushi,
Sakamoto Masami,
Sato Kazuki,
Yoshida Kazuhiro
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700217
Subject(s) - chemistry , benzene , catalysis , annulation , medicinal chemistry , organic chemistry , hydrazone , metathesis , polymerization , polymer
We have found that Suzuki–Miyaura‐type reactions of o ‐allyloxy(bromoethynyl)benzenes with arylboronic acids using a hydrazone/Cu catalyst system proceeded smoothly in i PrOH under mild conditions to afford the corresponding o ‐allyloxy(arylethynyl)benzene derivatives in good yields without decomposition of the allyloxy group. We have further demonstrated that annulation and enyne metathesis of the o ‐allyloxy(arylethynyl)benzene derivatives using transition‐metal catalysts led to various heterocyclic compounds.