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

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
› Author Affiliations
Further Information

Publication History

Received: 28 April 2013

Accepted after revision: 16 May 2013

Publication Date:
24 June 2013 (eFirst)

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%.

Supporting Information

Primary Data

 
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