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Title: Palladium-catalyzed double C - H functionalization of arenes at the positions ortho and meta to their directing group: Concise synthesis of benzocyclobutenes
Authors: Nanjo, Takeshi  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-5679-6701 (unconfirmed)
Tsukano, Chihiro  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0002-9361-0857 (unconfirmed)
Takemoto, Yoshiji  kyouindb  KAKEN_id  orcid https://orcid.org/0000-0003-1375-3821 (unconfirmed)
Author's alias: 南條, 毅
塚野, 千尋
竹本, 佳司
Keywords: C–H functionalization
benzocyclobutene
palladium
directing group
double functionalization
Issue Date: 1-Sep-2016
Publisher: Pharmaceutical Society of Japan
Journal title: Chemical and Pharmaceutical Bulletin
Volume: 64
Issue: 9
Start page: 1384
End page: 1392
Abstract: The synthesis of benzocyclobutenes from simple arenes bearing a directing group was investigated via the palladium-catalyzed cyclization of norbornene derivatives. This approach allowed for the facile construction of benzocyclobutenes along with the double functionalization of the C - H bonds at the positions ortho and meta to the directing group. This result shows that the key palladacyclopentene intermediate in the Catellani reaction can be prepared by the directed double ortho C - H activation of the substrate. The results of this study also revealed that the combination of an N-protected amino acid with benzoquinone (BQ) was effective for this transformation.
Rights: 許諾条件に基づいて掲載しています。
URI: http://hdl.handle.net/2433/235953
DOI(Published Version): 10.1248/cpb.c16-00439
Appears in Collections:Journal Articles

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