Synthesis 2013; 45(15): 2109-2114
DOI: 10.1055/s-0033-1339187
special topic
© Georg Thieme Verlag Stuttgart · New York

Highly Regioselective Allylic Substitution Reactions Catalyzed by an Air-Stable (π-Allyl)iridium Complex Derived from Dinaphthocyclooctatetraene and a Phosphoramidite Ligand

Authors

  • Ke-Yin Ye

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   eMail: slyou@sioc.ac.cn
  • Zhuo-An Zhao

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   eMail: slyou@sioc.ac.cn
  • Zeng-Wei Lai

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   eMail: slyou@sioc.ac.cn
  • Li-Xin Dai

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   eMail: slyou@sioc.ac.cn
  • Shu-Li You*

    State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. of China   Fax: +86(21)54925087   eMail: slyou@sioc.ac.cn
Weitere Informationen

Publikationsverlauf

Received: 28. April 2013

Accepted after revision: 16. Mai 2013

Publikationsdatum:
24. Juni 2013 (online)


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Abstract

An air-stable (π-allyl)iridium complex derived from dinaphthocyclooctatetraene and a phosphoramidite ligand has been synthesized and found to be highly efficient in iridium-catalyzed allylic substitution reactions. This catalyst features excellent regioselectivity and high stability. When NaCH(CO2Me)2 was used as the nucleophile, the catalyst loading in allylic alkylation reactions can be as low as 0.01 mol%.

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