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