Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction

Qianwen Gao; Ze-Shui Liu; Yu Hua; Siwei Zhou; Hong-Gang Cheng; Qianghui Zhou

doi:10.1055/s-0039-1690801

Synthesis, Table of Contents

Synthesis 2020; 52(06): 834-846
DOI: 10.1055/s-0039-1690801

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Alkyl Tosylates as Alkylating Reagents in the Catellani Reaction

Qianwen Gao

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn

,

Ze-Shui Liu

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn

,

Yu Hua

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn

,

Siwei Zhou

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn

,

Hong-Gang Cheng∗

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn

,

Qianghui Zhou∗

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), College of Chemistry and Molecular Sciences, Wuhan University, 430072 Wuhan, P. R. of China Email: hgcheng@whu.edu.cn Email: qhzhou@whu.edu.cn

^bThe Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China

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Abstract

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Abstract

A cooperative catalytic system involving a Pd/XPhos complex and inexpensive 5-norbornene-2-carbonitrile that enables the use of alkyl tosylates as alkylating reagents in the Catellani reaction has been developed. This mild, scalable protocol is compatible with a range of readily available functionalized aryl iodides and alkyl tosylates, as well as terminating olefins (45 examples, up to 97% yield).

Key words

Catellani reaction - cooperative catalysis - alkyl tosylates - 5-norbornene-2-carbonitrile - polysubstituted arenes

Full Text

References

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Supplementary Material

Supporting Information