HUSCAP logo Hokkaido Univ. logo

Hokkaido University Collection of Scholarly and Academic Papers >
Faculty of Pharmaceutical Sciences >
Peer-reviewed Journal Articles, etc >

Cp*Co-III Catalyzed Site-Selective C-H Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes

Files in This Item:
manuscript.pdf809.21 kBPDFView/Open
Please use this identifier to cite or link to this item:http://hdl.handle.net/2115/63311

Title: Cp*Co-III Catalyzed Site-Selective C-H Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes
Authors: Sun, Bo Browse this author
Yoshino, Tatsuhiko Browse this author →KAKEN DB
Kanai, Motomu Browse this author →KAKEN DB
Matsunaga, Shigeki Browse this author →KAKEN DB
Keywords: CH activation
cobalt
isoquinolines
transition-metal catalysis
Issue Date: 26-Oct-2015
Publisher: WILEY-VCH
Journal Title: Angewandte chemie-international edition
Volume: 54
Issue: 44
Start Page: 12968
End Page: 12972
Publisher DOI: 10.1002/anie.201507744
PMID: 26412390
Abstract: The synthesis of isoquinolines by site-selective CH activation of O-acyl oximes with a Cp*Co-III catalyst is described. In the presence of this catalyst, the CH activation of various unsymmetrically substituted O-acyl oximes selectively occurred at the sterically less hindered site, and reactions with terminal as well as internal alkynes afforded the corresponding products in up to 98% yield. Whereas the reactions catalyzed by the Cp*Co-III system proceeded with high site selectivity (15:1 to 20:1), use of the corresponding Cp*Rh-III catalysts led to low selectivities and/or yields when unsymmetrical O-acyl oximes and terminal alkynes were used. Deuterium labeling studies indicate a clear difference in the site selectivity of the CH activation step under Cp*Co-III and Cp*Rh-III catalysis.
Rights: This is the peer reviewed version of the following article: Sun, B., Yoshino, T., Kanai, M. and Matsunaga, S. (2015), Cp*CoIII Catalyzed Site-Selective C-H Activation of Unsymmetrical O-Acyl Oximes: Synthesis of Multisubstituted Isoquinolines from Terminal and Internal Alkynes. Angew. Chem. Int. Ed., 54: 12968-12972., which has been published in final form at http://dx.doi.org/10.1002/anie.201507744. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
Type: article (author version)
URI: http://hdl.handle.net/2115/63311
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 松永 茂樹

Export metadata:

OAI-PMH ( junii2 , jpcoar )

MathJax is now OFF:


 

 - Hokkaido University